Arylphenyl-substituted cyclic ketoenols

ABSTRACT

The present invention relates to novel arylphenyl-substituted cyclic ketoenols of the formula (I) 
                         
in which
         X represents halogen, alkyl, alkoxy, alkenyloxy, alkylthio, alkylsulphinyl, alkylsulphonyl, halogenoalkyl, halogenoalkoxy, halogenoalkenyloxy, nitro, cyano or in each case optionally substituted phenyl, phenoxy, phenylthio, phenylalkoxy or phenylalkylthio,   Y represents in each case optionally substituted cycloalkyl, aryl or hetaryl,   Z represents hydrogen, halogen, alkyl, alkoxy, alkenyloxy, halogenoalkyl, halogenoalkoxy, halogenoalkenyloxy, nitro or cyano,   CKE represents one of the groups       
     
       
         
         
             
             
         
       
         
         
           
              in which 
             A, B, D, G and Q 1  to Q 6  are each as defined in the description,
 
to a plurality of processes for their preparation and to their use as pesticides and herbicides.

This application is a divisional application of U.S. patent applicationSer. No. 10/137,763 filed May 2, 2002, now U.S. Pat. No. 6,716,832 forwhich a Notice of Allowance was issued Nov. 20, 2003, which in turn wasa divisional application of U.S. patent application Ser. No. 09/623,016filed Oct. 23, 2000, now U.S. Pat. No. 6,417,370 issued Jul. 9, 2002,which was the national stage of PCT/EP99/01029 filed Feb. 17, 1999,claiming priority of German Patent DE 198 08 261.4, filed Feb. 27, 1998.

The present invention relates to novel arylphenyl-substituted cyclicketoenols, to a plurality of processes for their preparation and totheir use as pesticides and herbicides.

Pharmaceutical properties of 3-acyl-pyrrolidine-2,4-diones have alreadybeen described (S. Suzuki et al. Chem. Pharm. Bull. 15 1120 (1967)).Furthermore, N-phenylpyrrolidine-2,4-diones have been synthesized by R.Schmierer and H. Mildenberger (Liebigs Ann. Chem. 1985, 1095). Abiological activity of these compounds has not been described.

EP-A-0 262 399 and GB-A-2 266 888 disclose compounds of a similarstructure (3-aryl-pyrrolidine-2,4-diones) of which, however, noherbicidal, insecticidal or acaricidal activity has become known.Unsubstituted bicyclic 3-aryl-pyrrolidine-2,4-dione derivatives(EP-A-355 599 and EP415 211) and substituted monocyclic3-aryl-pyrrolidine-2,4-dione derivatives (EP-A-377 893 and EP-442 077)having herbicidal, insecticidal or acaricidal activity are known.

Also known are polycyclic 3-arylpyrrolidine-2,4-dione derivatives(EP-442 073) and 1H-arylpyrrolidine-dione derivatives (EP-456 063,EP-521 334, EP-596 298, EP-613 884, EP-613 885, WO 94/01 997, WO 95/26954, WO 95/20 572, EP-A-0 668 267, WO 96/25 395, WO 96/35 664, WO 97/01535, WO 97/02 243 and WO 97/36 868, WO 98/05 638).

It is known that certain substituted Δ³-dihydrofuran-2-one derivativeshave herbicidal properties (cf. DE-A-4 014 420). The synthesis of thetetronic acid derivatives used as starting materials (such as, forexample,3-(2-methyl-phenyl)-4-hydroxy-5-(4-fluorophenyl)-Δ³-dihydrofuran-2-one)is likewise described in DE-A-4 014 420. Compounds of a similarstructure are known from the publication Campbell et al., J. Chem. Soc.,Perkin Trans. 1, 1985, (8) 1567–76, without any insecticidal and/oracaricidal activity being mentioned. Furthermore,3-aryl-Δ³-di-hydrofuranone derivatives having herbicidal, acaricidal andinsecticidal properties are known from EP-A-528 156, EP-A-0 647 637, WO95/26 345, WO 96/20 196, WO 96/25 395, WO 96/35 664, WO 97/01 535, WO97/02 243 and WO 97/36 868, WO 98/05 638. 3-Aryl-Δ³-dihydrothiophene-onederivatives are likewise known (WO 95/26 345, 96/25 395, WO 97/01 535,WO 97/02 243, WO 97/36 868, WO 98/05 638).

Also known from the literature are certain 3H-pyrazol-3-one derivatives,such as, for example,1,2-diethyl-1,2-dihydro-5-hydroxy-4-phenyl-3H-pyrazol-3-one or[5-oxo-1,2-diphenyl-4-(p-sulphophenyl)-3-pyrazolin-3-yl]-oxy, disodiumsalt, orp-(3-hydroxy-5-oxo-1,2-diphenyl-3-pyrazolin-4-yl)-benzenesulphonic acid(cf. J. Heterocycl. Chem., 25(5), 1301–1305, 1988 or J. Heterocycl.Chem., 25(5), 1307–1310, 1988 or Zh. Obshch. Khim., 34(7), 2397–2402,1964). However, a biological activity of these compounds is notdescribed.

Furthermore, it is known that the trisodium salt of4,4′,4″-(5-hydroxy-3-oxo-1H-pyrazol-1,2,4(3H)-triyl)-tris-benzenesulphonicacid has pharmacological properties (cf. Farmakol. Toksikol. (Moscow),38(2), 180–186, 1976). However, it is not known to be used in cropprotection.

Moreover, EP-508 126 and WO 92/16 510, WO 96/21 652 describe4-arylpyrazolidin-3,5-dione derivatives having herbicidal, acaricidaland insecticidal properties. Additionally, 4-arylpyrazolidines havebecome known of which fungicidal properties have been described (WO96/36 229, WO 96/36 615, WO 96/36 616, WO 96/36 633).

Certain phenyl-pyrone derivatives which are unsubstituted in the phenylring have already become known (cf. A. M. Chirazi, T. Kappe and E.Ziegler, Arch. Pharm. 309, 558 (1976) and K.-H. Boltze and K.Heidenbluth, Chem. Ber. 91, 2849), a possible use of these compounds aspesticides not being mentioned. Phenyl-pyrone derivatives which aresubstituted in the phenyl ring and have herbicidal, acaricidal andinsecticidal properties are described in EP-A-588 137, WO 96/25 395, WO96/35 664, WO 97/01 535, WO 97/02 243, WO 97/16 436, WO 97/19 941 and WO97/36 868, WO 98/05 638.

Certain 5-phenyl-1,3-thiazine derivatives which are unsubstituted in thephenyl ring have already become known (cf. E. Ziegler and E. Steiner,Monatsh. 95, 147 (1964), R. Ketcham, T. Kappe and E. Ziegler, J.Heterocycl. Chem. 10, 223 (1973)), a possible use of these compounds aspesticides not being mentioned. 5-Phenyl-1,3-thiazine derivatives whichare substituted in the phenyl ring and have herbicidal, acaricidal andinsecticidal activity are described in WO 94/14 785, WO 96/02 539, WO96/35 664, WO 97/01535, WO 97/02 243, WO 97/02 243, WO 97/36 868.

It is known that certain substituted 2-arylcyclopentanediones haveherbicidal and acaricidal properties (cf., for example, U.S. Pat. Nos.4,283,348; 4,338,122; 4,436,666; 4,526,723; 4,551,547; 4,632,698; WO96/01 798; WO 96/03 366 and also WO 97/14 667). Moreover, compounds of asimilar structure are known:3-hydroxy-5,5-dimethyl-2-phenylcyclopent-2-ene-1-one from thepublication Micklefield et al., Tetrahedron, (1992), 7519–26 and thenatural product involutine(−)-cis-5-(3,4-dihydroxyphenyl)-3,4-dihydroxy-2-(4-hydroxyphenyl)-cyclopent-2-ene-onefrom the publication Edwards et al., J. Chem. Soc. S, (1967), 405–9. Aninsecticidal or acaricidal activity is not described. Moreover,2-(2,4,6-trimethylphenyl)-1,3-indanedione is known from the publicationJ. Economic Entomology, 66, (1973), 584 and the Offenlegungsschrift DE-2361 084, with herbicidal and acaricidal activities being mentioned.

It is known that certain substituted 2-arylcyclohexanediones haveherbicidal and acaricidal properties (cf., for example, U.S. Pat. Nos.4,175,135, 4,209,432, 4,256,657, 4,256,658, 4,256,659, 4,257,858,4,283,348, 4,303,669, 4,351,666, 4,409,153, 4,436,666, 4,526,723,4,613,617, 4,659,372, DE-2 813 341, and also Wheeler, T. N., J. Org.Chem. 44, 4906 (1979)).

However, the activity and the activity spectrum of these compounds are,in particular at low application rates and concentrations, not alwaysentirely satisfactory. Furthermore, the compatibility of these compoundswith plants is not always satisfactory.

This invention, accordingly, provides novel compounds of the formula (I)

in which

-   X represents halogen, alkyl, alkoxy, alkenyloxy, alkylthio,    alkylsulphinyl, alkylsulphonyl, halogenoalkyl, halogenoalkoxy,    halogenoalkenyloxy, nitro, cyano or in each case optionally    substituted phenyl, phenoxy, phenylthio, phenylalkoxy or    phenylalkylthio,-   Y represents in each case optionally substituted cycloalkyl, aryl or    hetaryl,-   Z represents hydrogen, halogen, alkyl, alkoxy, alkenyloxy,    halogenoalkyl, halogenoalkoxy, halogenoalkenyloxy, nitro or cyano,-   CKE represents one of the groups

-   -   in which    -   A represents hydrogen, in each case optionally        halogen-substituted alkyl, alkenyl, alkoxyalkyl,        polyalkoxyalkyl, alkylthioalkyl, saturated or unsaturated,        optionally substituted cycloalkyl in which optionally at least        one ring atom is replaced by a heteroatom, or in each case        optionally halogen-, alkyl-, halogenoalkyl-, alkoxy,        halogenoalkoxy-, cyano- or nitro-substituted aryl, arylalkyl or        hetaryl,    -   B represents hydrogen, alkyl or alkoxyalkyl, or    -   A and B together with the carbon atom to which they are attached        represent a saturated or unsaturated unsubstituted or        substituted cycle which optionally contains at least one        heteroatom,    -   D represents hydrogen or an optionally substituted radical        selected from the series consisting of alkyl, alkenyl, alkinyl,        alkoxyalkyl, polyalkoxyalkyl, alkylthioalkyl, saturated or        unsaturated cycloalkyl in which one or more ring members are        optionally replaced by heteroatoms, arylalkyl, aryl,        hetarylalkyl or hetaryl or    -   A and D together with the atoms to which they are attached        represent a saturated or unsaturated cycle which is        unsubstituted or substituted in the A,D moiety and which        optionally contains at least one (in the case where CKE=(4)        further) heteroatom, or    -   A and Q¹ together represent alkanediyl or alkenediyl, each of        which is optionally substituted by in each case optionally        substituted alkyl, hydroxyl, alkoxy, alkylthio, cycloalkyl,        benzyloxy or aryl, or    -   Q¹ represents hydrogen or alkyl,    -   Q², Q⁴, Q⁵ and Q⁶ independently of one another each represent        hydrogen or alkyl,    -   Q³ represents hydrogen, alkyl, alkoxyalkyl, alkylthioalkyl,        optionally substituted cycloalkyl (in which optionally one        methylene group is replaced by oxygen or sulphur) or optionally        substituted phenyl, or    -   Q³ and Q⁴ together with the carbon atom to which they are        attached represent a saturated or unsaturated unsubstituted or        substituted cycle which optionally contains a heteroatom,    -   G represents hydrogen (a) or represents one of the groups

-   -   -   in which        -   E represents a metal ion or an ammonium ion,        -   L represents oxygen or sulphur,        -   M represents oxygen or sulphur,        -   R¹ represents in each case optionally halogen-substituted            alkyl, alkenyl, alkoxyalkyl, alkylthioalkyl, polyalkoxyalkyl            or optionally halogen-, alkyl- or alkoxy-substituted            cycloalkyl, in which one or more methylene groups can be            replaced with heteroatoms, in each case optionally            substituted phenyl, phenylalkyl, hetaryl, phenoxyalkyl or            hetaryloxyalkyl,        -   R² represents in each case optionally halogen-substituted            alkyl, alkenyl, alkoxyalkyl, polyalkoxyalkyl or represents            in each case optionally substituted cycloalkyl, phenyl or            benzyl,        -   R³, R⁴ and R⁵ independently of one another each represent in            each case optionally halogen-substituted alkyl, alkoxy,            alkylamino, dialkylamino, alkylthio, alkenylthio,            cycloalkylthio and represent in each case optionally            substituted phenyl, benzyl, phenoxy or phenylthio,        -   R⁶ and R⁷ independently of one another each represent            hydrogen, in each case optionally halogen-substituted alkyl,            cycloalkyl, alkenyl, alkoxy, alkoxyalkyl, represent            optionally substituted phenyl, represent optionally            substituted benzyl, or together with the nitrogen atom to            which they are attached represent a cycle which is            optionally interrupted by oxygen or sulphur.

Depending, inter alia, on the nature of the substituents, the compoundsof the formula (I) can be present as geometrical and/or optical isomersor mixtures of isomers in varying compositions, which can be separated,if desired, in a customary manner. The present invention provides boththe pure isomers and the isomer mixtures, their preparation and use andalso compositions comprising them. In the following, for simplicity,however, compounds of the formula (I) are always referred to, althoughboth pure compounds and, if appropriate, mixtures having differentproportions of isomeric compounds are intended.

Including the meanings (1) to (8) of the group CKE, the followingprincipal structures (I-1) to (I-8) result:

in which

-   A, B, D, G, Q¹, Q², Q³, Q⁴, Q⁵, Q⁶, X, Y and Z are each as defined    above.

Including the various meanings (a), (b), (c), (d), (e), (f) and (g) ofthe group G, the following principal structures (I-1-a) to (I-1-g),result if CKE represents the group (1),

in which

-   A, B, D, E, L, M, X, Y, Z, R¹, R², R³, R⁴, R⁵, R⁶ and R⁷ are each as    defined above.

Including the various meanings (a), (b), (c), (d), (e), (f) and (g) ofthe group G, the following principal structures (I-2-a) to (I-2-g),result if CKE represents the group (2),

in which

-   A, B, E, L, M, X, Y, Z, R¹, R², R³, R⁴, R⁵, R⁶ and R⁷ are each as    defined above.

Including the various meanings (a), (b), (c), (d), (e), (f) and (g) ofthe group G, the following principal structures (I-3-a) to (I-3-g),result if CKE represents the group (3),

in which

-   A, B, E, L, M, X, Y, Z, R¹, R², R³, R⁴, R⁵, R⁶ and R⁷ are each as    defined above.

Including the various meanings (a), (b), (c), (d), (e), (f) and (g) ofthe group G, the following principal structures (I-4-a) to (I-4-g),result if CKE represents the group (4),

in which

-   A, D, E, L, M, X, Y, Z, R¹, R², R³, R⁴, R⁵, R⁶ and R⁷ are each as    defined above.

Depending on the position of the substituent G, the compounds of theformula (I-5) can be present in the two isomeric forms of the formulae(I-5-A) and (I-5-B),

which is meant to be indicated by the dashed line in the formula (I-5).

The compounds of the formulae (I-5-A) and (I-5-B) can be present both asmixtures and in the form of their pure isomers. Mixtures of thecompounds of the formulae (I-5-A) and (I-5-B) can be separated, ifdesired, in a manner known per se by physical methods, for example bychromatographic methods.

For reasons of clarity, hereinbelow in each case only one of thepossible isomers is given. This does not exclude that the compounds may,if appropriate, be present in the form of the isomer mixtures or in therespective other isomeric form.

Including the various meanings (a), (b), (c), (d), (e), (f) and (g) ofthe group G, the following principal structures (I-5-a) to (I-5-g)result if CKE represents the group (5),

in which

-   A, D, E, L, M, X, Y, Z, R¹, R², R³, R⁴, R⁵, R⁶ and R⁷ are each as    defined above.

Including the various meanings (a), (b), (c), (d), (e), (f) and (g) ofthe group G, the following principal structures (I-6-a) to (I-6-g),result if CKE represents the group (6),

in which

-   A, E, L, M, X, Y, Z, R¹, R², R³, R⁴, R⁵, R⁶ and R⁷ are each as    defined above.

Depending on the position of the substituent G, the compounds of theformula (I-7) can be present in the two isomeric forms of the formulae(I-7-A) and (I-7-B):

which is meant to be indicated by the dashed line in the formula (I).

The compounds of the formulae (I-7-A) and (I-7-B) can be present both asmixtures and in the form of their pure isomers. Mixtures of thecompounds of the formulae (I-7-A) and (I-7-B) can be separated, ifdesired, by physical methods, for example by chromatographic methods.

For reasons of clarity, hereinbelow in each case only one of thepossible isomers is given. This does not exclude that the compounds may,if appropriate, be present in the form of the isomer mixtures or in therespective other isomeric form.

Including the various meanings (a), (b), (c), (d), (e), (f) and (g) ofthe group G, the following principal structures (I-7-a) to (I-7-g)result:

in which

-   A, B, Q¹, Q², E, L, M, X, Y, Z, R¹, R², R³, R⁴, R⁵, R⁶ and R⁷ are    each as defined above.

Depending on the position of the substituent G, the compounds of theformula (I-8) can be present in the two isomeric forms of the formulae(I-8-A) and (I-8-B)

which is meant to be indicated by the dashed line in the formula (I).

The compounds of the formulae (I-8-A) and (I-8-B) can be present both asmixtures and in the form of their pure isomers. Mixtures of thecompounds of the formulae (I-8-A) and (I-8-B) can be separated, ifdesired, by physical methods, for example by chromatographic methods.

For reasons of clarity, hereinbelow in each case only one of thepossible isomers is given. This takes into account that the relevantcompound may, if appropriate, be present as an isomer mixture or in therespective other isomeric form.

Including the various meanings (a), (b), (c), (d), (e), (f) and (g) ofthe group G, the following principal structures (I-8-a) to (I-8-g)result:

in which

-   A, B, E, L, M, Q³, Q⁴, Q⁵, Q⁶, X, Y, Z, R¹, R², R³, R⁴, R⁵, R⁶ and    R⁷ are each as defined above.

Furthermore, it has been found that the novel compounds of the formula(I) are obtained by one of the processes described below:

-   (A) Substituted 3-phenylpyrrolidine-2,4-diones or their enols of the    formula (I-1-a)

-   -   in which    -   A, B, D, X, Y and Z are each as defined above    -   are obtained when    -   N-acylamino acid esters of the formula (II)

-   -   in which    -   A, B, D, X, Y and Z are each as defined above and    -   R⁸ represents alkyl (preferably C₁–C₆-alkyl)    -   are condensed intramolecularly in the presence of a diluent and        in the presence of a base.

-   (B) Moreover, it has been found that substituted    3-phenyl-4-hydroxy-Δ³-dihydrofuranone derivatives of the formula    (I-2-a)

-   -   in which    -   A, B, X, Y and Z are each as defined above    -   are obtained when    -   carboxylic esters of the formula (III)

-   -   in which    -   A, B, X, Y, Z and R⁸ are each as defined above    -   are condensed intramolecularly in the presence of a diluent and        in the presence of a base.

-   (C) Furthermore, it has been found that substituted    3-phenyl-4-hydroxy-Δ³-dihydrothiophenone derivatives of the formula    (I-3-a)

-   -   in which    -   A, B, X, Y and Z are each as defined above    -   are obtained when    -   β-ketocarboxylic esters of the formula (IV)

-   -   in which    -   A, B, X, Y, Z and R⁸ are each as defined above and    -   W represents hydrogen, halogen (preferably fluorine, chlorine,        bromine), alkyl (preferably C₁–C₆-alkyl) or alkoxy (preferably        C₁–C₈-alkoxy)    -   are cyclized intramolecularly, if appropriate in the presence of        a diluent and in the presence of an acid.

-   (D) Furthermore, substituted 3-hydroxyl-4-phenyl-5-oxo-pyrazolines    of the formula (I-4-a)

-   -   in which    -   A, D, X, Y and Z are each as defined above    -   are obtained when

-   (α) halogenocarbonyl ketenes of the formula (V)

-   -   in which    -   X, Y and Z are each as defined above and    -   Hal represents halogen (in particular chlorine or bromine) or

-   (β) malonic acid derivatives of the formula (VI)

-    in which    -   R⁸, X, Y and Z are each as defined above    -   are reacted with hydrazines of the formula (VII)        A-NH—NH-D  (VII)    -   in which    -   A and D are each as defined above    -   if appropriate in the presence of a diluent and if appropriate        in the presence of a base.-   (E) Furthermore, it has been found that the novel substituted    3-phenylpyrone derivatives of the formula (I-5-a)

-   -   in which    -   A, D, X, Y and Z are each as defined above    -   are obtained when    -   carbonyl compounds of the formula (VIII)

-   -   in which    -   A and D are each as defined above    -   or their silyl enol ethers of the formula (VIIIa)

-   -   in which    -   A, D and R⁸ are each as defined above    -   are reacted with ketene acid halides of the formula (V)

-   -   in which    -   X, Y and Z are each as defined above and    -   Hal represents halogen (preferably represents chlorine or        bromine),    -   if appropriate in the presence of a diluent and if appropriate        in the presence of an acid acceptor.

Furthermore, it has been found

-   (F) that the novel substituted phenyl-1,3-thiazine derivatives of    the formula (I-6-a)

-   -   in which    -   A, X, Y and Z are each as defined above    -   are obtained when thioamides of the formula (IX)

-   -   in which    -   A is as defined above    -   are reacted with ketene acid halides of the formula (V)

-   -   in which    -   Hal, X, Y and Z are each as defined above,    -   if appropriate in the presence of a diluent and if appropriate        in the presence of an acid acceptor.

Furthermore, it has been found

-   (G) that compounds of the formula (I-7-a)

-   -   in which    -   A, B, Q¹, Q², X, Y and Z are each as defined above    -   are obtained when    -   ketocarboxylic esters of the formula (X)

-   -   in which    -   A, B, Q¹, Q², X, Y and Z are each as defined above and    -   R⁸ represents alkyl (in particular C₁–C₈-alkyl)    -   are cyclized intramolecularly, if appropriate in the presence of        a diluent and in the presence of a base.

Moreover, it has been found

-   (H) that compounds of the formula (I-8-a)

-   -   in which    -   A, B, Q³, Q⁴, Q⁵, Q⁶, X, Y and Z are each as defined above    -   are obtained when    -   6-aryl-5-keto-hexanoic esters of the formula (XI)

-   -   in which    -   A, B, Q³, Q⁴, Q⁵, Q⁶, X, Y and Z are each as defined above and    -   R⁸ represents alkyl (preferably C₁–C₆-alkyl)    -   are condensed intramolecularly in the presence of a diluent and        in the presence of a base; or

-   (I) that compounds of the formulae (I-1-a) to (I-8-a) shown above in    which A, B, D, Q¹, Q², Q³, Q⁴, Q⁵, Q⁶, X, Y and Z are each as    defined above are obtained when compounds of the formula (I-1′-a) to    (I-8′-a),

-   -   in which    -   A, B, D, Q¹, Q², Q³, Q⁴, Q⁵, Q⁶, X and Z are each as defined        above and    -   Y′ represents chlorine, bromine or iodine, preferably represents        bromine, are reacted with boronic acids of the formula (XII)

-   -   in which    -   Y is as defined above    -   in the presence of a solvent, a base and a catalyst, suitable        catalysts being, in particular, palladium complexes.

Moreover, it has been found

-   (J) that the compounds of the formulae (I-1-b) to (I-8-b) shown    above in which A, B, D, Q¹, Q², Q³, Q⁴, Q⁵, Q⁶, R¹, X, Y and Z are    each as defined above are obtained when compounds of the formulae    (I-1-a) to (I-8-a) shown above in which A, B, D, Q¹, Q², Q³, Q⁴, Q⁵,    Q⁶, X, Y and Z are each as defined above are in each case-   (α) reacted with acyl halides of the formula (XIII)

-   -   in which    -   R¹ is as defined above and    -   Hal represents halogen (in particular chlorine or bromine) or

-   (β) reacted with carboxylic anhydrides of the formula (XIV)    R¹—CO—O—CO—R¹  (XIV)    -   in which    -   R¹ is as defined above,    -   if appropriate in the presence of a diluent and if appropriate        in the presence of an acid binder;

-   (K) that the compounds of the formulae (I-1-c) to (I-8-c) shown    above in which A, B, D, Q¹, Q², Q³, Q⁴, Q⁵, Q⁶, R², M, X, Y and Z    are each as defined above and L represents oxygen are obtained when    compounds of the formulae (I-1-a) to (I-8-a) shown above in which A,    B, D, Q¹, Q², Q³, Q⁴, Q⁵, Q⁶, X, Y and Z are each as defined above    are in each case    -   reacted with chloroformic esters or chloroformic thioesters of        the formula (XV)        R²-M-CO—Cl  (XV)    -   in which    -   R² and M are each as defined above,    -   if appropriate in the presence of a diluent and if appropriate        in the presence of an acid binder;

-   (L) that compounds of the formulae (I-1-c) to (I-8-c) shown above in    which A, B, D, Q¹, Q², Q³, Q⁴, Q⁵, Q⁶, R², M, X, Y and Z are each as    defined above and L represents sulphur are obtained when compounds    of the formulae (I-1-a) to (I-8-a) shown above in which A, B, D, Q¹,    Q², Q³, Q⁴, Q⁵, Q⁶, X, Y and Z are each as defined above are in each    case reacted with chloromonothioformic esters or chlorodithioformic    esters of the formula (XVI)

-    in which    -   M and R² are each as defined above    -   if appropriate in the presence of a diluent and if appropriate        in the presence of an acid binder and-   (M) that compounds of the formulae (I-1-d) to (I-8-d) shown above in    which A, B, D, Q¹, Q², Q³, Q⁴, Q⁵, Q⁶, R³, X, Y and Z are each as    defined above are obtained when compounds of the formulae (I-1-a) to    (I-8-a) shown above in which A, B, D, Q¹, Q², Q³, Q⁴, Q⁵, Q⁶, X, Y    and Z are each as defined above are in each case    -   reacted with sulphonyl chlorides of the formula (XVII)        R³—SO₂—Cl  (XVII)    -   in which    -   R³ is as defined above,    -   if appropriate in the presence of a diluent and if appropriate        in the presence of an acid binder,-   (N) that compounds of the formulae (I-1-e) to (I-8-e) shown above in    which A, B, D, L, Q¹, Q², Q³, Q⁴, Q⁵, Q⁶, R⁴, R⁵, X, Y and Z are    each as defined above are obtained when compounds of the formulae    (I-1-a) to (I-8-a) shown above in which A, B, D, Q¹, Q², Q³, Q⁴, Q⁵,    Q⁶, X, Y and Z are each as defined above are in each case    -   reacted with phosphorus compounds of the formula (XVIII)

-   -   in which    -   L, R⁴ and R⁵ are each as defined above and    -   Hal represents halogen (in particular chlorine or bromine),    -   if appropriate in the presence of a diluent and if appropriate        in the presence of an acid binder,

-   (L) that compounds of the formulae (I-1-f) to (I-8-f) shown above in    which A, B, D, E, Q¹, Q², Q³, Q⁴, Q⁵, Q⁶, X, Y and Z are each as    defined above are obtained when compounds of the formulae (I-1-a) to    (I-8-a) in which A, B, D, Q¹, Q², Q³, Q⁴, Q⁵, Q⁶, X, Y and Z are    each as defined above are in each case    -   reacted with metal compounds or amines of the formulae (XIX) or        (XX)        Me(OR¹⁰)_(t)  (XIX)

-    in which    -   Me represents a mono- or divalent metal (preferably an alkali        metal or alkaline earth metal, such as lithium, sodium,        potassium, magnesium or calcium),    -   t represents the number 1 or 2 and    -   R¹⁰, R¹¹, R¹² independently of one another each represent        hydrogen or alkyl (preferably C₁–C₈-alkyl),    -   if appropriate in the presence of a diluent,-   (P) that compounds of the formulae (I-1-g) to (I-8-g) shown above in    which A, B, D, L, Q¹, Q², Q³, Q⁴, Qs, Q⁶, R⁶, R⁷, X, Y and Z are    each as defined above are obtained when compounds of the formulae    (I-1-a) to (I-8-a) shown above in which A, B, D, Q¹, Q², Q³, Q⁴, Q⁵,    Q⁶, X, Y and Z are each as defined above are in each case-   (α) reacted with isocyanates or isothiocyanates of the formula (XXI)    R⁶—N═C=L  (XXI)    -   in which    -   R⁶ and L are each as defined above    -   if appropriate in the presence of a diluent and if appropriate        in the presence of a catalyst, or-   (β) reacted with carbamoyl chlorides or thiocarbamoyl chlorides of    the formula (XXII)

-   -   in which    -   L, R⁶ and R⁷ are each as defined above    -   if appropriate in the presence of a diluent and if appropriate        in the presence of an acid binder.

Furthermore, it has been found that the novel compounds of the formula(I) have very good activity as pesticides, preferably as insecticides,acaricides and also as herbicides.

The formula (I) provides a general definition of the compounds accordingto the invention. Preferred substituents or ranges of the radicalslisted in the formulae mentioned hereinabove and hereinbelow areillustrated below:

-   X preferably represents halogen, C₁–C₆-alkyl, C₁–C₆-halogenoalkyl,    C₁–C₆-alkoxy, C₃–C₆-alkenyloxy, C₁–C₆-alkylthio,    C₁–C₆-alkylsulphinyl, C₁–C₆-alkylsulphonyl, C₁–C₆-halogenoalkoxy,    C₃–C₆-halogenoalkenyloxy, nitro, cyano or in each case optionally    halogen-, C₁–C₆-alkyl-, C₁–C₆-alkoxy-, C₁–C₄-halogenoalkyl-,    C₁–C₄-halogenoalkoxy-, nitro- or cyano-substituted phenyl, phenoxy,    phenylthio, benzyloxy or benzylthio.-   Y preferably represents one of the radicals

-   V¹ preferably represents hydrogen, halogen, C₁–C₁₂-alkyl,    C₁–C₆-alkoxy, C₁–C₄-halogenoalky, C₁–C₄-halogenoalkoxy, nitro, cyano    or phenyl, phenoxy, phenoxy-C₁–C₄-alkyl, phenyl-C₁–C₄-alkoxy,    phenylthio-C₁–C₄-alkyl or phenyl-C₁–C₄-alkylthio, each of which is    optionally mono- or polysubstituted by halogen, C₁–C₆-alkyl,    C₁–C₆-alkoxy, C₁–C₄-halogenoalkyl, C₁–C₄-halogenoalkoxy, nitro or    cyano.-   V² and V³ independently of one another each preferably represent    hydrogen, halogen, C₁–C₆-alkyl, C₁–C₆-alkoxy, C₁–C₄-halogenoalkyl or    C₁–C₄-halogenoalkoxy.-   Z preferably represents hydrogen, halogen, C₁–C₆-alkyl,    C₁–C₆-halogenoalkyl, C₁–C₆-alkoxy, C₁–C₆-halogenoalkoxy, nitro or    cyano.-   CKE preferably represents one of the groups

-   A preferably represents hydrogen or in each case optionally    halogen-substituted C₁–C₁₂-alkyl, C₃–C₈-alkenyl,    C₁–C₁₀-alkoxy-C₁–C₈-alkyl, poly-C₁–C₈-alkoxy-C₁–C₈-alkyl,    C₁–C₁₀-alkylthio-C₁–C₆-alkyl, optionally halogen-, C₁–C₆-alkyl- or    C₁–C₆-alkoxy-substituted C₃–C₈-cycloalkyl in which optionally one or    two not directly adjacent ring members are replaced by oxygen and/or    sulphur or represents in each case optionally halogen-,    C₁–C₆-alkyl-, C₁–C₆-halogenoalkyl-, C₁–C₆-alkoxy-,    C₁–C₆-halogenoalkoxy-, cyano- or nitro-substituted C₆- or C₁₀-aryl    (phenyl or naphthyl), hetaryl having 5 to 6 ring atoms (for example    furanyl, pyridyl, imidazolyl, triazolyl, pyrazolyl, pyrimidyl,    thiazolyl or thienyl) or C₆- or C₁₀-aryl-C₁–C₆-alkyl    (phenyl-C₁–C₆-alkyl or naphthyl-C₁–C₆-alkyl).-   B preferably represents hydrogen, C₁–C₁₂-alkyl or    C₁–C₈-alkoxy-C₁–C₆-alkyl or-   A, B and the carbon atom to which they are attached preferably    represent saturated C₃–C₁₀-cycloalkyl or unsaturated    C₅–C₁₀-cycloalkyl in which optionally one ring member is replaced by    oxygen or sulphur and which are optionally mono- or disubstituted by    C₁–C₈-alkyl, C₃–C₁₀-cycloalkyl, C₁–C₈-halogenoalkyl, C₁–C₈-alkoxy,    C₁–C₈-alkylthio, halogen or phenyl or-   A, B and the carbon atom to which they are attached preferably    represent C₃–C₆-cycloalkyl which is substituted by an alkylenedilyl    group which optionally contains one or two not directly adjacent    oxygen and/or sulphur atoms, or by an alkylenedioxyl group or by an    alkylenedithioyl group which, together with the carbon atom to which    it is attached, forms a further five- to eight-membered ring, or-   A, B and the carbon atom to which they are attached preferably    represent C₃–C₈-cycloalkyl or C₅–C₈-cycloalkenyl, in which two    substituents together with the carbon atoms to which they are    attached represent in each case optionally C₁–C₆-alkyl-,    C₁–C₆-alkoxy- or halogen-substituted C₂–C₆-alkanediyl,    C₂–C₆-alkenediyl or C₄–C₆-alkanedienediyl in which optionally one    methylene group is replaced by oxygen or sulphur.-   D preferably represents hydrogen, in each case optionally    halogen-substituted C₁–C₁₂-alkyl, C₃–C₈-alkenyl, C₃–C₈-alkinyl,    C₁–C₁₀-alkoxy-C₂–C₈-alkyl, poly-C₁–C₈-alkoxy-C₂–C₈-alkyl,    C₁–C₁₀-alkylthio-C₂–C₈-alkyl, optionally halogen-, C₁–C₄-alkyl-,    C₁–C₄-alkoxy- or C₁–C₄-halogenoalkyl-substituted C₃–C₈-cycloalkyl in    which optionally one ring member is replaced by oxygen or sulphur or    in each case optionally halogen-, C₁–C₆-alkyl-,    C₁–C₆-halogenoalkyl-, C₁–C₆-alkoxy-, C₁–C₆-halogenoalkoxy-, cyano-    or nitro-substituted phenyl, hetaryl having 5 or 6 ring atoms (for    example furanyl, imidazolyl, pyridyl, thiazolyl, pyrazolyl,    pyrimidyl, pyrrolyl, thienyl or triazolyl), phenyl-C₁–C₆-alkyl or    hetaryl-C₁–C₆-alkyl having 5 or 6 ring atoms (for example furanyl-,    imidazolyl-, pyridyl-, thiazolyl-, pyrazolyl-, pyrimidyl-,    pyrrolyl-, thienyl- or triazolyl-C₁–C₆-alkyl), or-   A and D together preferably represent in each case optionally    substituted C₃–C₆-alkanediyl or C₃–C₆-alkenediyl in which optionally    one methylene group is replaced by oxygen or sulphur,    -   possible substituents in each case being:    -   halogen, hydroxyl, mercapto or in each case optionally        halogen-substituted C₁–C₁₀-alkyl, C₁–C₆-alkoxy, C₁–C₆-alkylthio,        C₃–C₇-cycloalkyl, phenyl or benzyloxy, or a further        C₃–C₆-alkanediyl grouping, C₃–C₆-alkenediyl grouping or a        butadienyl grouping which is optionally substituted by        C₁–C₆-alkyl or in which optionally two adjacent substituents        together with the carbon atoms to which they are attached form a        further saturated or unsaturated cycle having 5 or 6 ring atoms        (in the case of the compound of the formula (I-1), A and D,        together with the atoms to which they are attached, then        represent, for example, the groups AD-1 to AD-10 mentioned        further below) which cycle may contain oxygen or sulphur, or        which may optionally contain one of the groups below

-   A and Q¹ together preferably represent C₃–C₆-alkanediyl or    C₄–C₆-alkenediyl, each of which is optionally mono- or disubstituted    by identical or different substituents selected from the group    consisting of halogen, hydroxyl; C₁–C₁-alkyl, C₁–C₆-alkoxy,    C₁–C₆-alkylthio, C₃–C₇-cycloalkyl, each of which is optionally mono-    to trisubstituted by identical or different halogens; and benzyloxy    and phenyl, each of which is optionally mono- to trisubstituted by    identical or different substituents selected from the group    consisting of halogen, C₁–C₆-alkyl or C₁–C₆-alkoxy, and which    furthermore optionally contains one of the groups below

-    or is bridged by a C₁–C₂-alkanediyl group or by an oxygen atom, or-   Q¹ preferably represents hydrogen or C₁–C₄-alkyl.-   Q², Q⁴, Q⁵ and Q⁶ independently of one another each preferably    represent hydrogen or C₁–C₄-alkyl,-   Q³ preferably represents hydrogen, C₁–C₆-alkyl,    C₁–C₆-alkoxy-C₁–C₂-alkyl, C₁–C₆-alkylthio-C₁–C₂-alkyl, optionally    C₁–C₄-alkyl- or C₁–C₄-alkoxy-substituted C₃–C₈-cycloalkyl in which    optionally one methylene group is replaced by oxygen or sulphur or    optionally halogen-, C₁–C₄-alkyl-, C₁–C₄-alkoxy-,    C₁–C₂-halogenoalkyl-, C₁–C₂-halogenoalkoxy-, cyano- or    nitro-substituted phenyl, or-   Q³ and Q⁴ together with the carbon atom to which they are attached    represent optionally C₁–C₄-alkyl-, C₁–C₄-alkoxy- or    C₁–C₂-halogenoalkyl-substituted C₃–C₇-cycloalkyl in which optionally    one ring member is replaced by oxygen or sulphur.-   G preferably represents hydrogen (a) or represents one of the groups

in particular represents (a), (b) or (c),

-   -   in which    -   E represents a metal ion or an ammonium ion,    -   L represents oxygen or sulphur and    -   M represents oxygen or sulphur.

-   R¹ preferably represents in each case optionally halogen-substituted    C₁–C₂₀-alkyl, C₂–C₂₀-alkenyl, C₁–C₈-alkoxy-C₁–C₈-alkyl,    C₁–C₈-alkylthio-C₁–C₈-alkyl, poly-C₁–C₈-alkoxy-C₁–C₈-alkyl or    optionally halogen-, C₁–C₆-alkyl- or C₁–C₆-alkoxy-substituted    C₃–C₈-cycloalkyl in which optionally one or more (preferably one or    two) not directly adjacent ring members are replaced by oxygen    and/or sulphur,    -   represents optionally halogen-, cyano-, nitro-, C₁–C₆-alkyl-,        C₁–C₆-alkoxy-, C₁–C₆-halogenoalkyl-, C₁–C₆-halogenoalkoxy-,        C₁–C₆-alkylthio- or C₁–C₆-alkylsulphonyl-substituted phenyl,    -   represents optionally halogen-, nitro-, cyano-, C₁–C₆-alkyl-,        C₁–C₆-alkoxy-, C₁–C₆-halogenoalkyl- or        C₁–C₆-halogenoalkoxy-substituted phenyl-C₁–C₆-alkyl,    -   represents optionally halogen- or C₁–C₆-alkyl-substituted 5- or        6-membered hetaryl (for example pyrazolyl, thiazolyl, pyridyl,        pyrimidyl, furanyl or thienyl),    -   represents optionally halogen- or C₁–C₆-alkyl-substituted        phenoxy-C₁–C₆-alkyl or    -   represents optionally halogen-, amino- or        C₁–C₆-alkyl-substituted 5- or 6-membered hetaryloxy-C₁–C₆-alkyl        (for example pyridyloxy-C₁–C₆-alkyl, pyrimidyloxy-C₁–C₆-alkyl or        thiazolyloxy-C₁–C₆-alkyl).

-   R² preferably represents in each case optionally halogen-substituted    C₁–C₂₀-alkyl, C₂–C₂₀-alkenyl, C₁–C₈-alkoxy-C₂–C₈-alkyl,    poly-C₁–C₈-alkoxy-C₂–C₈-alkyl,    -   represents optionally halogen-, C₁–C₆-alkyl- or        C₁–C₆-alkoxy-substituted C₃–C₈-cycloalkyl or    -   represents in each case optionally halogen-, cyano-, nitro-,        C₁–C₆-alkyl-, C₁–C₆-alkoxy-, C₁–C₆-halogenoalkyl- or        C₁–C₆-halogenoalkoxy-substituted phenyl or benzyl.

-   R³ preferably represents optionally halogen-substituted C₁–C₈-alkyl    or represents in each case optionally halogen-, C₁–C₆-alkyl-,    C₁–C₆-alkoxy-, C₁–C₄-halogenoalkyl-, C₁–C₄-halogenoalkoxy-, cyano-    or nitro-substituted phenyl or benzyl.

-   R⁴ and R⁵ independently of one another each preferably represent in    each case optionally halogen-substituted C₁–C₈-alkyl, C₁–C₈-alkoxy,    C₁–C₈-alkylamino, di-(C₁–C₈-alkyl)amino, C₁–C₈-alkylthio,    C₂–C₈-alkenylthio, C₃–C₇-cycloalkylthio or represent in each case    optionally halogen-, nitro-, cyano-, C₁–C₄-alkoxy-,    C₁–C₄-halogenoalkoxy-, C₁–C₄-alkylthio-, C₁–C₄-halogenoalkylthio-,    C₁–C₄-alkyl- or C₁–C₄-halogenoalkyl-substituted phenyl, phenoxy or    phenylthio.

-   R⁶ and R⁷ independently of one another each preferably represent    hydrogen, represent in each case optionally halogen-substituted    C₁–C₈-alkyl, C₃–C₈-cycloalkyl, C₁–C₈-alkoxy, C₃–C₈-alkenyl,    C₁–C₈-alkoxy-C₁–C₈-alkyl, represent optionally halogen-,    C₁–C₈-halogenoalkyl-, C₁–C₈-alkyl- or C₁–C₈-alkoxy-substituted    phenyl, optionally halogen-, C₁–C₈-alkyl-, C₁–C₈-halogenoalkyl- or    C₁–C₈-alkoxy-substituted benzyl or together represent an optionally    C₁–C₄-alkyl-substituted C₃–C₆-alkylene radical in which optionally    one carbon atom is replaced by oxygen or sulphur.

-   R¹³ preferably represents hydrogen, represents in each case    optionally halogen-substituted C₁–C₈-alkyl or C₁–C₈-alkoxy,    represents optionally halogen-, C₁–C₄-alkyl- or    C₁–C₄-alkoxy-substituted C₃–C₈-cycloalkyl in which optionally one    methylene group is replaced by oxygen or sulphur, or represents in    each case optionally halogen-, C₁–C₆-alkyl-, C₁–C₆-alkoxy-,    C₁–C₄-halogenoalkyl-, C₁–C₄-halogenoalkoxy-, nitro- or    cyano-substituted phenyl, phenyl-C₁–C₄-alkyl or phenyl-C₁–C₄-alkoxy.

-   R¹⁴ preferably represents hydrogen or C₁–C₈-alkyl, or

-   R¹³ and R¹⁴ together preferably represent C₄–C₆-alkanediyl.

-   R¹⁵ and R¹⁶ are identical or different and each preferably represent    C₁–C₆-alkyl, or

-   R¹⁵ and R¹⁶ together preferably represent a C₂–C₄-alkanediyl radical    which is optionally substituted by C₁–C₆-alkyl, C₁–C₆-halogenoalkyl    or by optionally halogen-, C₁–C₆-alkyl-, C₁–C₄-halogenoalkyl-,    C₁–C₆-alkoxy-, C₁–C₄-halogenoalkoxy-, nitro- or cyano-substituted    phenyl.

-   R¹⁷ and R¹⁸ independently of one another each preferably represent    hydrogen, represent optionally halogen-substituted C₁–C₈-alkyl or    represent optionally halogen-, C₁–C₆-alkyl-, C₁–C₆-alkoxy-,    C₁–C₄-halogenoalkyl-, C₁–C₄-halogenoalkoxy-, nitro- or    cyano-substituted phenyl, or

-   R¹⁷ and R¹⁸ together with the carbon atom to which they are attached    preferably represent a carbonyl group or represent optionally    halogen-, C₁–C₄-alkyl- or C₁–C₄-alkoxy-substituted C₅–C₇-cycloalkyl    in which optionally one methylene group is replaced by oxygen or    sulphur.

-   R¹⁹ and R²⁰ independently of one another each preferably represent    C₁–C₁₀-alkyl, C₂–C₁₀-alkenyl, C₁–C₁₀-alkoxy, C₁–C₁₀-alkylamino,    C₃–C₁₀-alkenylamino, di-(C₁–C₁₀-alkyl)amino or    di-(C₃–C₁₀-alkenyl)amino.

In the preferred radical definitions, halogen, including as substituent,such as, for example, in halogenoalkyl, represents fluorine, chlorine,bromine and iodine and in particular represents fluorine and chlorine.

-   X particularly preferably represents fluorine, chlorine, bromine,    C₁–C₄-alkyl, C₁–C₄-alkoxy, C₃–C₄-alkenyloxy, C₁–C₄-halogenoalkyl,    C₁–C₄-halogenoalkoxy, C₃–C₄-halogenoalkenyloxy, nitro or cyano.-   Y particularly preferably represents one of the radicals

-   V¹ particularly preferably represents hydrogen, fluorine, chlorine,    bromine, C₁–C₆-alkyl, C₁–C₄-alkoxy, C₁–C₂-halogenoalkyl,    C₁–C₂-halogenoalkoxy, nitro, cyano or phenyl, phenoxy,    phenoxy-C₁–C₂-alkyl, phenyl-C₁–C₂-alkoxy, phenylthio-C₁–C₂-alkyl or    phenyl-C₁–C₂-alkylthio, each of which is optionally mono- or    disubstituted by fluorine, chlorine, bromine, C₁–C₄-alkyl,    C₁–C₄-alkoxy, C₁–C₂-halogenoalkyl, C₁–C₂-halogenoalkoxy, nitro or    cyano.-   V² and V³ independently of one another each particularly preferably    represent hydrogen, fluorine, chlorine, bromine, C₁–C₄-alkyl,    C₁–C₄-alkoxy, C₁–C₂-halogenoalkyl or C₁–C₂-halogenoalkoxy.-   Z particularly preferably represents hydrogen, fluorine, chlorine,    bromine, C₁–C₄-alkyl, C₁–C₄-halogenoalkyl, C₁–C₄-alkoxy or    C₁–C₄-halogenoalkoxy.-   CKE particularly preferably represents one of the groups

-   A particularly preferably represents hydrogen, in each case    optionally fluorine- or chlorine-substituted C₁–C₁₀-alkyl,    C₁–C₈-alkoxy-C₁–C₆-alkyl, optionally fluorine-, chlorine-,    C₁–C₄-alkyl- or C₁–C₄-alkoxy-substituted C₃–C₇-cycloalkyl in which    optionally one ring member is replaced by oxygen or sulphur or (but    not in the case of the compounds of the formulae (I-5), (I-7) and    (I-8)) in each case optionally fluorine-, chlorine-, bromine-,    C₁–C₄-alkyl-, C₁–C₄-halogenoalkyl-, C₁–C₄-alkoxy- or    C₁–C₄-halogenoalkoxy-substituted phenyl, furanyl, pyridyl,    imidazolyl, triazolyl, pyrazolyl, pyrimidyl, thiazolyl, thienyl or    phenyl-C₁–C₄-alkyl.-   B particularly preferably represents hydrogen or C₁–C₆-alkyl, or-   A, B and the carbon atom to which they are attached particularly    preferably represent saturated or unsaturated C₅–C₇-cycloalkyl in    which optionally one ring member is replaced by oxygen or sulphur    and which is optionally monosubstituted by C₁–C₆-alkyl,    C₅–C₈-cycloalkyl, C₁–C₃-halogenoalkyl, C₁–C₆-alkoxy, fluorine,    chlorine or phenyl, or-   A, B and the carbon atom to which they are attached particularly    preferably represent C₅–C₆-cycloalkyl which is substituted by an    alkylenediyl group which optionally contains one or two not directly    adjacent oxygen or sulphur atoms or by an alkylenedioxyl group or by    an alkylenedithiol group which, together with the carbon atom to    which it is attached, forms a further five- or six-membered ring, or-   A, B and the carbon atom to which they are attached particularly    preferably represent C₃–C₆-cycloalkyl or C₅–C₆-cycloalkenyl in which    two substituents together with the carbon atoms to which they are    attached represent in each case optionally C₁–C₅-alkyl-,    C₁–C₅-alkoxy-, fluorine-, chlorine- or bromine-substituted    C₂–C₄-alkanediyl, C₂–C₄-alkenediyl, in which optionally one    methylene group is replaced by oxygen or sulphur, or butadienediyl.-   D particularly preferably represents hydrogen, represents in each    case optionally fluorine- or chlorine-substituted C₁–C₁₀-alkyl,    C₃–C₆-alkenyl, C₁–C₈-alkoxy-C₂–C₆-alkyl or    C₁–C₈-alkylthio-C₂–C₆-alkyl, represents optionally fluorine-,    chlorine-, C₁–C₄-alkyl-, C₁–C₄-alkoxy- or    C₁–C₂-halogenoalkyl-substituted C₃–C₇-cycloalkyl in which optionally    one methylene group is replaced by oxygen or sulphur or (but not in    the case of the compounds of the formulae (I-1) and (I-4))    represents in each case optionally fluorine-, chlorine-, bromine-,    C₁–C₄-alkyl-, C₁–C₄-halogenoalkyl-, C₁–C₄-alkoxy- or    C₁–C₄-halogenoalkoxy-substituted phenyl, furanyl, imidazolyl,    pyridyl, thiazolyl, pyrazolyl, pyrimidyl, pyrrolyl, thienyl,    triazolyl or phenyl-C₁–C₄-alkyl, or-   A and D together particularly preferably represent optionally    substituted C₃–C₅-alkanediyl in which one methylene group may be    replaced by a carbonyl group, oxygen or sulphur, possible    substituents being hydroxyl, C₁–C₆-alkyl or C₁–C₄-alkoxy, or-   A and D (in the case of the compounds of the formula (I-1)) together    with the atoms to which they are attached represent one of the    groups AD-1 to AD-10:

-   A and Q¹ together particularly preferably represent C₃–C₄-alkanediyl    or C₃–C₄-alkenediyl, each of which is optionally mono- or    disubstituted by identical or different substituents selected from    the group consisting of fluorine, chlorine, hydroxyl, and    C₁–C₈-alkyl and C₁–C₄-alkoxy, each of which is optionally mono- to    trisubstituted by fluorine, or-   Q¹ particularly preferably represents hydrogen.-   Q² particularly preferably represents hydrogen.-   Q⁴, Q⁵ and Q⁶ independently of one another each particularly    preferably represent hydrogen or C₁–C₃-alkyl.-   Q³ particularly preferably represents hydrogen, C₁–C₄-alkyl,    C₁–C₄-alkoxy-C₁–C₂-alkyl, C₁–C₄-alkylthio-C₁–C₂-alkyl or optionally    methyl- or methoxy-substituted C₃–C₆-cycloalkyl in which optionally    one methylene group is replaced by oxygen or sulphur, or-   Q³ and Q⁴ together with the carbon atom to which they are attached    particularly preferably represent an optionally C₁–C₄-alkyl- or    C₁–C₄-alkoxy-substituted saturated C₅–C₆-cycloalkyl in which    optionally one ring member is replaced by oxygen or sulphur.-   G particularly preferably represents hydrogen (a) or particularly    preferably represents one of the groups

-    in particular represents (a), (b) or (c),    -   in which    -   E represents a metal ion or an ammonium ion,    -   L represents oxygen or sulphur and    -   M represents oxygen or sulphur.-   R¹ particularly preferably represents in each case optionally    fluorine- or chlorine-substituted C₁–C₁₆-alkyl, C₂–C₁₆-alkenyl,    C₁–C₆-alkoxy-C₁–C₆-alkyl, C₁–C₆-alkylthio-C₁–C₆-alkyl,    poly-C₁–C₆-alkoxy-C₁–C₆-alkyl or optionally fluorine-, chlorine-,    C₁–C₅-alkyl- or C₁–C₅-alkoxy-substituted C₃–C₇-cycloalkyl in which    optionally one or two not directly adjacent ring members are    replaced by oxygen and/or sulphur,    -   represents optionally fluorine-, chlorine-, bromine-, cyano-,        nitro-, C₁–C₄-alkyl-, C₁–C₄-alkoxy-, C₁–C₃-halogenoalkyl-,        C₁–C₃-halogenoalkoxy-, C₁–C₄-alkylthio- or        C₁–C₄-alkylsulphonyl-substituted phenyl,    -   represents optionally fluorine-, chlorine-, bromine-,        C₁–C₄-alkyl-, C₁–C₄-alkoxy-, C₁–C₃-halogenoalkyl- or        C₁–C₃-halogenoalkoxy-substituted phenyl-C₁–C₄-alkyl,    -   represents in each case optionally fluorine-, chlorine-,        bromine- or C₁–C₄-alkyl-substituted pyrazolyl, thiazolyl,        pyridyl, pyrimidyl, furanyl or thienyl,    -   represents optionally fluorine-, chlorine-, bromine- or        C₁–C₄-alkyl-substituted phenoxy-C₁–C₃-alkyl or    -   represents in each case optionally fluorine-, chlorine-,        bromine-, amino- or C₁–C₄-alkyl-substituted        pyridyloxy-C₁–C₃-alkyl, pyrimidyloxy-C₁–C₃-alkyl or        thiazolyloxy-C₁–C₃-alkyl.-   R² particularly preferably represents in each case optionally    fluorine-substituted C₁–C₁₆-alkyl, C₂–C₁₆-alkenyl,    C₁–C₆-alkoxy-C₂–C₆-alkyl or poly-C₁–C₆-alkoxy-C₂–C₆-alkyl,    -   represents optionally fluorine-, chlorine-, C₁–C₄-alkyl- or        C₁–C₄-alkoxy-substituted C₃–C₇-cycloalkyl or    -   represents in each case optionally fluorine-, chlorine-,        bromine-, cyano-, nitro-, C₁–C₄-alkyl-, C₁–C₃-alkoxy-,        C₁–C₃-halogenoalkyl- or C₁–C₃-halogenoalkoxy-substituted phenyl        or benzyl,-   R³ particularly preferably represents optionally    fluorine-substituted C₁–C₆-alkyl or particularly preferably    represents in each case optionally fluorine-, chlorine-, bromine-,    C₁–C₄-alkyl-, C₁–C₄-alkoxy-, C₁–C₃-halogenoalkyl-,    C₁–C₃-halogenoalkoxy-, cyano- or nitro-substituted phenyl or benzyl,-   R⁴ and R⁵ independently of one another each particularly preferably    represent C₁–C₆-alkyl, C₁–C₆-alkoxy, C₁–C₆-alkylamino,    di-(C₁–C₆-alkyl)amino, C₁–C₆-alkylthio, C₃–C₄-alkenylthio,    C₃–C₆-cycloalkylthio or represent in each case optionally fluorine-,    chlorine-, bromine-, nitro-, cyano-, C₁–C₃-alkoxy-,    C₁–C₃-halogenoalkoxy-, C₁–C₃-alkylthio-, C₁–C₃-halogenoalkylthio-,    C₁–C₃-alkyl- or C₁–C₃-halogenoalkyl-substituted phenyl, phenoxy or    phenylthio, and-   R⁶ and R⁷ independently of one another each particularly preferably    represent hydrogen, C₁–C₆-alkyl, C₃–C₆-cycloalkyl, C₁–C₆-alkoxy,    C₃–C₆-alkenyl, C₁–C₆-alkoxy-C₁–C₆-alkyl, represent optionally    fluorine-, chlorine-, bromine-, C₁–C₃-halogenoalkyl-, C₁–C₄-alkyl-    or C₁–C₄-alkoxy-substituted phenyl, represent optionally fluorine-,    chlorine-, bromine-, C₁–C₄-alkyl-, C₁–C₃-halogenoalkyl- or    C₁–C₄-alkoxy-substituted benzyl, or together represent an optionally    methyl- or ethyl-substituted C₄–C₅-alkylene radical in which    optionally one methylene group is replaced by oxygen or sulphur.

In the particularly preferred radical definitions, halogen, including assubstituent, such as, for example, in halogenoalkyl, representsfluorine, chlorine, bromine and iodine, in particular representsfluorine, chlorine and bromine and very particularly represents fluorineor chlorine.

-   X very particularly preferably represents fluorine, chlorine,    methyl, ethyl, n-propyl, iso-propyl, methoxy, ethoxy, n-propoxy,    iso-propoxy, trifluoromethyl, difluoromethoxy, trifluoromethoxy,    nitro or cyano (with emphasis on fluorine, chlorine, methyl, ethyl,    n-propyl or iso-propyl).-   Y very particularly preferably represents one of the radicals

-    in particular represents

-   V¹ very particularly preferably represents hydrogen, fluorine,    chlorine, bromine, methyl, ethyl, n-propyl, iso-propyl, n-butyl,    iso-butyl, tert-butyl, methoxy, ethoxy, n-propoxy, iso-propoxy,    trifluoromethyl, trifluoromethoxy, nitro, cyano or phenyl.-   V² and V³ independently of one another each very particularly    preferably represent hydrogen, fluorine, chlorine, methyl, ethyl,    n-propyl, iso-propyl, methoxy, ethoxy, trifluoromethyl or    trifluoromethoxy.-   Z very particularly preferably represents hydrogen, fluorine,    chlorine, methyl, ethyl, n-propyl, methoxy, ethoxy or n-propoxy    (with emphasis on hydrogen, fluorine, chlorine, methyl, ethyl or    n-propyl).-   CKE very particularly preferably represents one of the groups

-   A very particularly preferably represents hydrogen, in each case    optionally fluorine-substituted C₁–C₈-alkyl or    C₁–C₆-alkoxy-C₁–C₄-alkyl, optionally fluorine-, methyl-, ethyl- or    methoxy-substituted C₃–C₆-cycloalkyl in which optionally one ring    member is replaced by oxygen or sulphur or (but not in the case of    the compounds of the formulae (I-5), (I-7) and (I-8)) represents in    each case optionally fluorine-, chlorine-, bromine-, methyl-,    ethyl-, n-propyl-, iso-propyl-, methoxy-, ethoxy-, trifluoromethyl-,    trifluoromethoxy-, cyano- or nitro-substituted phenyl or benzyl.-   B very particularly preferably represents C₁–C₄-alkyl, or-   A, B and the carbon atom to which they are attached very    particularly preferably represent saturated C₅–C₆-cycloalkyl in    which optionally one ring member is replaced by oxygen or sulphur    and which is optionally monosubstituted by methyl, ethyl, n-propyl,    isopropyl, butyl, iso-butyl, sec-butyl, tert-butyl, trifluoromethyl,    methoxy, ethoxy, n-propoxy, iso-propoxy, n-butoxy, isobutoxy,    sec-butoxy, tert-butoxy, fluorine or chlorine, or-   A, B and the carbon atom to which they are attached very    particularly preferably represent C₅–C₆-cycloalkyl in which two    substituents together with the carbon atoms to which they are    attached represent C₂–C₄-alkanediyl or C₂–C₄-alkenediyl in which in    each case optionally one methylene group is replaced by oxygen or    sulphur, or butadienediyl.-   D very particularly preferably represents hydrogen, represents in    each case optionally fluorine- or chlorine-substituted C₁–C₈-alkyl,    C₃–C₄-alkenyl, C₁–C₆-alkoxy-C₂–C₄-alkyl, C₁–C₄-alkylthio-C₂–C₄-alkyl    or C₃–C₆-cycloalkyl in which optionally one methylene group is    replaced by oxygen or sulphur or (but not in the case of the    compounds of the formulae (I-1) and (I-4)) represents in each case    optionally fluorine-, chlorine-, methyl-, ethyl-, n-propyl-,    iso-propyl-, methoxy-, ethoxy-, trifluoromethyl- or    trifluoromethoxy-substituted phenyl, furanyl, pyridyl, thienyl or    benzyl (in compounds of the formula (I-1) with emphasis on    hydrogen), or-   A and D together very particularly preferably represent optionally    substituted C₃–C₄-alkanediyl in which optionally one carbon atom is    replaced by sulphur and which is optionally substituted by hydroxyl,    methyl, ethyl, methoxy or ethoxy, or-   A and D (in the case of the compounds of the formula (I-1)) together    with the atoms to which they are attached represent one of the    following groups AD:

-   A and Q¹ together very particularly preferably represent    C₃–C₄-alkanediyl or butenediyl, each of which is optionally mono- or    disubstituted by fluorine, hydroxyl, methyl or methoxy, or-   Q¹ very particularly preferably represents hydrogen.-   Q² very particularly preferably represents hydrogen.-   Q⁴, Q⁵ and Q⁶ independently of one another each very particularly    preferably represent hydrogen, methyl or ethyl.-   Q³ very particularly preferably represents hydrogen, methyl, ethyl    or C₃–C₆-cycloalkyl in which optionally one methylene group is    replaced by oxygen or sulphur (with emphasis on hydrogen, methyl or    ethyl), or-   Q³ and Q⁴ together with the carbon to which they are attached very    particularly preferably represent optionally methyl- or    methoxy-substituted saturated C₅–C₆-cycloalkyl in which optionally    one ring member is replaced by oxygen or sulphur.-   G very particularly preferably represents hydrogen (a) or represents    one of the groups

in particular represents (a), (b) or (c),

-   -   in which    -   E represents a metal ion or an ammonium ion,    -   L represents oxygen or sulphur and    -   M represents oxygen or sulphur.

-   R¹ very particularly preferably represents in each case optionally    fluorine- or chlorine-substituted C₁–C₁₄-alkyl, C₂–C₁₄-alkenyl,    C₁–C₄-alkoxy-C₁–C₆-alkyl C₁–C₄-alkylthio-C₁–C₆-alkyl,    poly-C₁–C₄-alkoxy-C₁–C₄-alkyl or optionally fluorine-, chlorine-,    methyl-, ethyl-, n-propyl-, i-propyl-, n-butyl-, i-butyl-,    tert-butyl-, methoxy-, ethoxy-, n-propoxy- or    iso-propoxy-substituted C₃–C₆-cycloalkyl in which optionally one or    two not directly adjacent ring members are replaced by oxygen and/or    sulphur,    -   represents optionally fluorine-, chlorine-, bromine-, cyano-,        nitro-, methyl-, ethyl-, n-propyl-, i-propyl-, methoxy-,        ethoxy-, trifluoromethyl-, trifluoromethoxy-, methylthio-,        ethylthio-, methylsulphonyl- or ethylsulphonyl-substituted        phenyl,    -   represents optionally fluorine-, chlorine-, bromine-, methyl-,        ethyl-, n-propyl-, i-propyl-, methoxy-, ethoxy-,        trifluoromethyl- or trifluoromethoxy-substituted benzyl,    -   represents in each case optionally fluorine-, chlorine-,        bromine-, methyl- or ethyl-substituted furanyl, thienyl,        pyridyl, pyrimidyl, thiazolyl or pyrazolyl,    -   represents optionally fluorine-, chlorine-, methyl- or        ethyl-substituted phenoxy-C₁–C₂-alkyl or    -   represents in each case optionally fluorine-, chlorine-, amino-,        methyl- or ethyl-substituted pyridyloxy-C₁–C₂-alkyl,        pyrimidyloxy-C₁–C₂-alkyl or thiazolyloxy-C₁–C₂-alkyl.

-   R² very particularly preferably represents in each case optionally    fluorine-substituted C₁–C₁₄-alkyl, C₂–C₁₄-alkenyl,    C₁–C₄-alkoxy-C₂–C₆-alkyl or poly-C₁–C₄-alkoxy-C₂–C₆-alkyl,    -   represents optionally fluorine-, chlorine-, methyl-, ethyl-,        n-propyl-, isopropyl- or methoxy-substituted C₃–C₆-cycloalkyl,    -   or represents in each case optionally fluorine-, chlorine-,        cyano-, nitro-, methyl-, ethyl-, n-propyl-, i-propyl-, methoxy-,        ethoxy-, trifluoromethyl- or trifluoromethoxy-substituted phenyl        or benzyl.

-   R³ very particularly preferably represents in each case optionally    fluorine-substituted methyl, ethyl, n-propyl, isopropyl or in each    case optionally fluorine-, chlorine-, bromine-, methyl-,    tert-butyl-, methoxy-, trifluoromethyl-, trifluoromethoxy-, cyano-    or nitro-substituted phenyl or benzyl,

-   R⁴ and R⁵ independently of one another each very particularly    preferably represent C₁–C₄-alkyl, C₁–C₄-alkoxy, C₁–C₄-alkylamino,    di-(C₁–C₄-alkyl)amino, C₁–C₄-alkylthio or represent in each case    optionally fluorine-, chlorine-, bromine-, nitro-, cyano-,    C₁–C₂-alkoxy-, C₁–C₂-fluoroalkoxy-, C₁–C₂-alkylthio-,    C₁–C₂-fluoroalkylthio- or C₁–C₃-alkyl-substituted phenyl, phenoxy or    phenylthio.

-   R⁶ and R⁷ independently of one another each very particularly    preferably represent hydrogen, represent C₁–C₄-alkyl,    C₃–C₆-cycloalkyl, C₁–C₄-alkoxy, C₃–C₄-alkenyl,    C₁–C₄-alkoxy-C₁–C₄-alkyl, represent optionally fluorine-, chlorine-,    bromine-, trifluoromethyl-, methyl- or methoxy-substituted phenyl,    represent optionally fluorine-, chlorine-, bromine-, methyl-,    trifluoromethyl- or methoxy-substituted benzyl, or together    represent a C₅–C₆-alkylene radical in which optionally one methylene    group is replaced by oxygen or sulphur.

The abovementioned general or preferred radical definitions orillustrations can be combined with each other as desired, i.e. includingcombinations between the respective ranges and preferred ranges. Theyapply both to the end products and, correspondingly, to the precursorsand intermediates.

Preference according to the invention is given to the compounds of theformula (I) which contain a combination of the meanings listed above asbeing preferred (preferable).

Particular preference according to the invention is given to thecompounds of the formula (I) which contain a combination of the meaningslisted above as being particularly preferred.

Very particular preference according to the invention is given to thecompounds of the formula (I) which contain a combination of the meaningslisted above as being very particularly preferred.

Compounds of the formula (I) in which G represents hydrogen areparticularly preferred.

Saturated or unsaturated hydrocarbon radicals such as alkyl or alkenylmay in each case be straight-chain or branched as far as this ispossible, including in combination with heteroatoms, such as, forexample, in alkoxy.

Unless stated otherwise, optionally substituted radicals may be mono- orpolysubstituted, and in the case of polysubstitutions the substituentsmay be identical or different.

Besides the compounds mentioned in the Preparation Examples, thefollowing compounds of the formula (I-1-a) may be specificallymentioned:

TABLE 1

X = CH₃, Z = CH₃, V¹ = H, V² = H. A B D CH₃ H H C₂H₅ H H C₃H₇ H H i-C₃H₇H H C₄H₉ H H i-C₄H₉ H H s-C₄H₉ H H t-C₄H₉ H H CH₃ CH₃ H C₂H₅ CH₃ H C₃H₇CH₃ H i-C₃H₇ CH₃ H C₄H₉ CH₃ H i-C₄H₉ CH₃ H s-C₄H₉ CH₃ H t-C₄H₉ CH₃ HC₂H₅ C₂H₅ H C₃H₇ C₃H₇ H

CH₃ H

CH₃ H

CH₃ H —(CH₂)₂— H —(CH₂)₄— H —(CH₂)₅— H —(CH₂)₆— H —(CH₂)₇— H—(CH₂)₂—O—(CH₂)₂— H —CH₂—O—(CH₂)₃— H —(CH₂)₂—S—(CH₂)₂— H—CH₂—CHCH₃—(CH₂)₃— H —(CH₂)₂—CHCH₃—(CH₂)₂— H —(CH₂)₂—CHC₂H₅—(CH₂)₂— H—(CH₂)₂—CHC₃H₇—(CH₂)₂— H —(CH₂)₂—CHi-C₃H₇—(CH₂)₂— H—(CH₂)₂—CHOCH₃—(CH₂)₂— H —(CH₂)₂—CHOC₂H₅—(CH₂)₂— H—(CH₂)₂—CHOC₃H₇—(CH₂)₂— H —(CH₂)₂—CHi-C₃H₇—(CH₂)₂— H—(CH₂)₂—C(CH₃)₂—(CH₂)₂— H —CH₂—(CHCH₃)₂—(CH₂)₂— H

H

H

H

H

H A D B —(CH₂)₃— H —(CH₂)₄— H —CH₂—CHCH₃—CH₂— H —CH₂—CH₂—CHCH₃— H—CH₂—CHCH₃—CHCH₃— H —CH₂—S—CH₂— H —CH₂—S—(CH₂)₂— H —(CH₂)₂—S—CH₂— H

H H CH₃ H H C₂H₅ H H C₃H₇ H H i-C₃H₇ H H

H H

H H

H CH₃ CH₃ H CH₃ C₂H₅ H CH₃ C₃H₇ H CH₃ i-C₃H₇ H CH₃

H CH₃

H CH₃

H C₂H₅ CH₃ H C₂H₅ C₂H₅ H

TABLE 2 A, B and D are each as given in Table 1 X = C₂H₅; Z = CH₃; V¹ =H; V² = H.

TABLE 3 A, B and D are each as given in Table 1 X = C₂H₅; Z = C₂H₅; V¹ =H; V² = H.

TABLE 4 A, B and D are each as given in Table 1 X = CH₃; Z = CH₃; V¹ =4-Cl; V² = H.

TABLE 5 A, B and D are each as given in Table 1 X = C₂H₅; Z = CH₃; V¹ =4-Cl; V² = H.

TABLE 6 A, B and D are each as given in Table 1 X = C₂H₅; Z = C₂H₅; V¹ =4-Cl; V² = H.

TABLE 7 A, B and D are each as given in Table 1 X = CH₃; Z = CH₃ ; V¹ =3-Cl; V² = H.

TABLE 8 A, B and D are each as given in Table 1 X = C₂H₅; Z = CH₃; V¹ =3-Cl; V² = H.

TABLE 9 A, B and D are each as given in Table 1 X = C₂H₅; Z = C₂H₅; V¹ =3-Cl; V² = H.

TABLE 10 A, B and D are each as given in Table 1 X = CH₃; Z = CH₃; V¹ =2-Cl; V² = 4-Cl.

TABLE 11 A, B and D are each as given in Table 1 X = C₂H₅; Z = CH₃; V¹ =2-Cl; V² = 4-Cl.

TABLE 12 A, B and D are each as given in Table 1 X = C₂H₅; Z = C₂H₅; V¹= 2-Cl; V² = 4-Cl.

TABLE 13 A, B and D are each as given in Table 1 X = CH₃; Z = CH₃; V¹ =4-CF₃; V² = H.

TABLE 14 A, B and D are each as given in Table 1 X = C₂H₅; Z = CH₃; V¹ =4-CF₃; V² = H.

TABLE 15 A, B and D are each as given in Table 1 X = C₂H₅; Z = C₂H₅; V¹= 4-CF₃; V² = H.

TABLE 16 A, B and D are each as given in Table 1 X = CH₃; Z = CH₃; V¹ =4-CH₃; V² = H.

TABLE 17 A, B and D are each as given in Table 1 X = C₂H₅; Z = CH₃; V¹ =4-CH₃; V² = H.

TABLE 18 A, B and D are each as given in Table 1 X = C₂H₅; Z = C₂H₅; V¹= 4-CH₃; V² = H.

TABLE 19 A, B and D are each as given in Table 1 X = CH₃; Z = CH₃; V¹ =4-OCH₃; V² = H.

TABLE 20 A, B and D are each as given in Table 1 X = C₂H₅; Z = CH₃; V¹ =4-OCH₃; V² = H.

TABLE 21 A, B and D are each as given in Table 1 X = C₂H₅; Z = C₂H₅; V¹= 4-OCH₃; V² = H.

Besides the compounds mentioned in the Preparation Examples, thefollowing compounds of the formula (I-2-a) may be specificallymentioned:

TABLE 22

X = CH₃, Z = CH₃, V¹ = H, V² = H. A B CH₃ H C₂H₅ H C₃H₇ H i-C₃H₇ H C₄H₉H i-C₄H₉ H s-C₄H₉ H t-C₄H₉ H CH₃ CH₃ C₂H₅ CH₃ C₃H₇ CH₃ i-C₃H₇ CH₃ C₄H₉CH₃ i-C₄H₉ CH₃ s-C₄H₉ CH₃ t-C₄H₉ CH₃ C₂H₅ C₂H₅ C₃H₇ C₃H₇

CH₃

CH₃

CH₃ —(CH₂)₂— —(CH₂)₄— —(CH₂)₅— —(CH₂)₆— —(CH₂)₇— —(CH₂)₂—O—(CH₂)₂——CH₂—O—(CH₂)₃— —(CH₂)₂—S—(CH₂)₂— —CH₂—CHCH₃—(CH₂)₃——(CH₂)₂—CHCH₃—(CH₂)₂— (CH₂)₂—CHC₂H₅—(CH₂)₂— —(CH₂)₂—CHC₃H₇—(CH₂)₂——(CH₂)₂—CHi—C₃H₇—(CH₂)₂— —(CH₂)₂—CHOCH₃—(CH₂)₂— —(CH₂)₂—CHOC₂H₅—(CH₂)₂——(CH₂)₂—CHOC₃H₇—(CH₂)₂— —(CH₂)₂—CHi-C₃H₇—(CH₂)₂— —(CH₂)₂—C(CH₃)₂—(CH₂)₂——CH₂—(CHCH₃)₂—(CH₂)₂—

TABLE 23 A and B are each as given in Table 22 X = C₂H₅; Z = CH₃; V¹ =H; V² = H.

TABLE 24 A and B are each as given in Table 22 X = C₂H₅; Z = C₂H₅; V¹ =H; V² = H.

TABLE 25 A and B are each as given in Table 22 X = CH₃; Z = CH₃; V¹ =4-Cl; V² = H.

TABLE 26 A and B are each as given in Table 22 X = C₂H₅; Z = CH₃; V¹ =4-Cl; V² = H.

TABLE 27 A and B are each as given in Table 22 X = C₂H₅; Z = C₂H₅; V¹ =4-Cl; V² = H.

TABLE 28 A and B are each as given in Table 22 X = CH₃; Z = CH₃; V¹ =3-Cl; V² = H.

TABLE 29 A and B are each as given in Table 22 X = C₂H₅; Z = CH₃; V¹ =3-Cl; V² = H.

TABLE 30 A and B are each as given in Table 22 X = C₂H₅; Z = C₂H₅; V¹ =3-Cl; V² = H.

TABLE 31 A and B are each as given in Table 22 X = CH₃; Z = CH₃; V¹ =4-CF₃; V² = H.

TABLE 32 A and B are each as given in Table 22 X = C₂H₅; Z = CH₃; V¹ =4-CF₃; V² = H.

TABLE 33 A and B are each as given in Table 22 X = C₂H₅; Z = C₂H₅; V¹ =4-CF₃; V² = H.

TABLE 34 A and B are each as given in Table 22 X = CH₃; Z = CH₃; V¹ =2-Cl; V² = 4-Cl.

TABLE 35 A and B are each as given in Table 22 X = C₂H₅; Z = CH₃; V¹ =2-Cl; V² = 4-Cl.

TABLE 36 A and B are each as given in Table 22 X = C₂H₅; Z = C₂H₅; V¹ =2-Cl; V¹ = 4-Cl.

TABLE 37 A and B are each as given in Table 22 X = CH₃; Z = CH₃; V¹ =4-CH₃; V² = H.

TABLE 38 A and B are each as given in Table 22 X = C₂H₅; Z = CH₃; V¹ =4-CH₃; V² = H.

TABLE 39 A and B are each as given in Table 22 X = C₂H₅; Z = C₂H₅; V¹ =4-CH₃; V² = H.

TABLE 40 A and B are each as given in Table 22 X = CH₃; Z = CH₃; V¹ =4-OCH₃; V² = H.

TABLE 41 A and B are each as given in Table 22 X = C₂H₅; Z = CH₃; V¹ =4-OCH₃; V² = H.

TABLE 42 A and B are each as given in Table 22 X = C₂H₅; Z = C₂H₅; V¹ =4-OCH₃; V² = H.

Using, in accordance with process (A), ethylN-[(2-methyl-4-phenyl)-phenylacetyl]-1-amino-cyclohexane-carboxylate asstarting material, the course of the process according to the inventioncan be represented by the following equation:

Using, in accordance with process (B), ethyl(B)O-[(2-chloro-4-(4-chloro)-phenyl)phenylacetyl]-2-hydroxyisobutyrate,the course of the process according to the invention can be representedby the following equation:

Using, in accordance with process (C), ethyl2-[(2,6-dimethyl-4-phenyl)-phenyl]-4-(4-methoxy)-benzylmercapto-4-methyl-3-oxo-valerate,the course of the process according to the invention can be representedby the following equation:

Using, for example in accordance with process (D-α), chlorocarbonyl3-[(2-chloro-6-methyl-4-(4-methyl)-phenyl)-phenyl] ketene and1,2-diazacyclopentane as starting materials, the course of the processaccording to the invention can be represented by the following equation:

Using, for example in accordance with process (D-β), diethyl3-[2-methyl-4-(3-chloro-phenyl)]-phenylmalonate and1,2-diazacyclopentane as starting materials, the course of the processaccording to the invention can be represented by the following equation:

Using, for example in accordance with process (E), chlorocarbonyl2-[(2-ethyl-6-methyl-(4-trifluoromethoxy-phenyl))-phenyl] ketene andacetone as starting materials, the course of the process according tothe invention can be represented by the following equation:

Using, for example in accordance with process (F), chlorocarbonyl2-[(2,6-dimethyl-4-phenyl)-phenyl] ketene and thiobenzamide as startingmaterials, the course of the process according to the invention can berepresented by the following equation:

Using, in accordance with process (G), ethyl5-[(2-chloro-6-methyl-4-phenyl)phenyl]-2,3-tetramethylene-4-oxo-valerate,the course of the process according to the invention can be representedby the following equation:

Using, in accordance with process (H), ethyl5-[(2,6-dichloro-4-phenyl)-phenyl]-2,2-dimethyl-5-oxo-hexanoate, thecourse of the process according to the invention can be represented bythe following equation:

Using, in accordance with process (I),3-[(2,6-dimethyl-4-bromo)-phenyl]-4,4-(pentamethylene)-pyrrolidine-2,4-dioneand 4-chlorophenylboronic acid as starting materials, the course of thereaction can be represented by the following scheme:

Using, in accordance with process (Jα),3-[(2-chloro-4-(3-chloro-phenyl))-phenyl]-5,5-dimethylpyrrolidine-2,4-dioneand pivaloyl chloride as starting materials, the course of the processaccording to the invention can be represented by the following equation:

Using, in accordance with process (J), (variant β),3-[(2-ethyl-4-(4-methoxyphenyl))-phenyl]4-hydroxy-5-phenyl-Δ³-dihydrofuran-2-oneand acetic anhydride as starting materials, the course of the processaccording to the invention can be represented by the following equation:

Using, in accordance with process (K),8-[(2,6-diethyl-4-phenyl)-phenyl]-1,6-diazabicyclo-(4.3.0^(1.6))-nonane-7,9-dioneand ethoxyethyl chloroformate as starting materials, the course of theprocess according to the invention can be represented by the followingequation:

Using, in accordance with process (L),3-[(2-chloro-4-(4-fluoro-phenyl))-phenyl]-4-hydroxy-5-methyl-6-(3-pyridyl)-pyroneand methyl chloromonothioformate as starting materials, the course ofthe reaction can be represented as follows:

Using, in accordance with process (M),2-[(2,6-dimethyl-4-(4-methyl-phenyl))-phenyl]-5,5-pentamethylene-pyrrolidine-2,4-dioneand methanesulphonyl chloride as starting materials, the course of thereaction can be represented by the following equation:

Using, in accordance with process (N),2-[(2-methyl-4-phenyl)-phenyl]-4-hydroxy-5,5-dimethyl-Δ³-dihydrofuran-2-oneand 2,2,2-trifluoroethyl methanethiophosphonyl chloride as startingmaterials, the course of the reaction can be represented by thefollowing equation:

Using, in accordance with process (O),3-[(2-trifluoromethyl-4-(4-(4-trifluoromethylphenyl))-phenyl]-5-cyclopropyl-5-methyl-pyrrolidine-2,4-dioneand NaOH as components, the course of the process according to theinvention can be represented by the following equation:

Using, in accordance with process (P), variant α,3-[(2-methyl-4-(3-trifluoromethylphenyl))-phenyl]-4-hydroxy-5-tetramethylene-Δ³-dihydro-furan-2-oneand ethyl isocyanate as starting materials, the course of the reactioncan be represented by the following equation:

Using, in accordance with process (P), variant β,3-[(2-chloro-4-phenyl)-phenyl]-5-methyl-pyrrolidine-2,4-dione anddimethylcarbamoyl chloride as starting materials, the course of thereaction can be represented by the following scheme:

The compounds of the formula (II)

in which

-   A, B, D, X, Y, Z and R⁸ are each as defined above-   which are required as starting materials in the process (a)    according to the invention are novel.

The acylamino acid esters of the formula (II) are obtained, for example,when amino acid derivatives of the formula (XXIII)

in which

-   A, B, R⁸ and D are each as defined above-   are acylated with substituted phenylacetyl halides of the formula    (XXIV)

in which

-   X, Y and Z are each as defined above and-   Hal represents chlorine or bromine    (Chem. Reviews 52, 237–416 (1953); Bhattacharya, Indian J. Chem. 6,    341–5, 1968) or when acylamino acids of the formula (XXV)

in which

-   A, B, D, X, Y and Z are each as defined above-   are esterified (Chem. Ind. (London) 1568 (1968)).

The compounds of the formula (XXV)

in which

-   A, B, D, X, Y and Z are each as defined above are novel.

The compounds of the formula (XXV) are obtained when amino acids of theformula (XXVI)

in which

-   A, B and D are each as defined above-   are acylated with substituted phenylacetyl halides of the formula    (XXIV)

in which

-   X, Y and Z are each as defined above and-   Hal represents chlorine or bromine,    for example according to Schotten-Baumann (Organikum, VEB Deutscher    Verlag der Wissenschaften, Berlin 1977, p. 505).

The compounds of the formula (XXIV) are novel. They can be prepared byprocessses which are known in principle (see, for example, H. Henecka,Houben-Weyl, Methoden der Organischen Chemie, Vol. 8, p. 467–469(1952)).

The compounds of the formula (XXIV) are obtained, for example, byreacting substituted phenylacetic acids of the formula (XXVII)

in which

-   X, Y and Z are each as defined above-   with halogenating agents (for example thionyl chloride, thionyl    bromide, oxalyl chloride, phosgene, phosphorus trichloride,    phosphorus tribromide or phosphorus pentachloride), if appropriate    in the presence of a diluent (for example optionally chlorinated    aliphatic or aromatic hydrocarbons such as toluene or methylene    chloride), at temperatures from −20° C. to 150° C., preferably from    −10° C. to 100° C.

Some of the compounds of the formulae (XXIII) and (XXVI) are known,and/or they can be prepared by known processes (see, for example,Compagnon, Miocque Ann. Chim. (Paris) [14] 5, p. 11–22, 23–27 (1970)).

The substituted cyclic aminocarboxylic acids of the formula (XXVIa) inwhich A and B form a ring are generally obtainable by the Bucherer-Bergssynthesis or by the Strecker synthesis and are in each case obtained indifferent isomer forms. Thus, under the conditions of the Bucherer-Bergssynthesis, the isomers (for simplicity called β below), in which theradicals R and the carboxyl group are equatorial are predominantlyobtained, while under the conditions of the Strecker synthesis theisomers (for simplicity called α below) in which the amino group and theradicals R are equatorial are predominantly obtained.

(L. Munday, J. Chem. Soc. 4372 (1961); J. T. Eward, C. Jitrangeri, Can.J. Chem. 53, 3339 (1975).

Furthermore, the starting materials of the formula (II)

in which

-   A, B, D, X, Y, Z and R⁸ are each as defined above-   used in the above process (A) can be prepared when aminonitriles of    the formula (XXVIII)

in which

-   A, B and D are each as defined above are reacted with substituted    phenylacetyl halides of the formula (XXIV)

in which

-   X, Y, Z and Hal are each as defined above-   to give compounds of the formula (XXIX)

in which

-   A, B, D, X, Y and Z are each as defined above-   and these are subsequently subjected to acidic alcoholysis.

The compounds of the formula (XXIX) are likewise novel

The compounds of the formula (III)

in which

-   A, B, X, Y, Z and R⁸ are each as defined above-   required as starting materials in the process (B) according to the    invention are novel.

They can be prepared by methods known in principle.

Thus, the compounds of the formula (III), for example, are obtained when2-hydroxycarboxylic esters of the formula (XXX)

in which

-   A, B and R⁸ are each as defined above-   are acylated with substituted phenylacetyl halides of the formula    (XXIV)

in which

-   X, Y, Z and Hal are each as defined above    (Chem. Reviews 52, 237–416 (1953)).

Furthermore, compounds of the formula (III) are obtained whensubstituted phenylacetic acids of the formula (XXVII)

in which

-   X, Y and Z are each as defined above-   are alkylated with α-halogenocarboxylic esters of the formula (XXXI)

in which

-   A, B and R⁸ are each as defined above and-   Hal represents chlorine or bromine.

The compounds of the formula (XXVII) are novel.

The compounds of the formula (XXXI) are known and in most casescommercially available.

The compounds of the formula (XXVII)

in which

-   X, Y and Z are each as defined above-   are obtained, for example,-   α) when compounds of the formula (XXVII-a)

-   -   in which    -   X and Z are each as defined above    -   Y′ represents chlorine or bromine, preferably represents        bromine,    -   are reacted with boronic acids of the formula (XII)

-   -   in which    -   Y is as defined above    -   in the presence of a solvent, a base and a catalyst (preferably        a palladium complex, such as, for example,        tetrakis(triphenylphosphine)-palladium or

-   β) when phenylacetic esters of the formula (XXXII)

-   -   in which    -   X, Y, Z and R⁸ are each as defined above    -   are hydrolysed under generally known standard conditions in the        presence of acids or bases, in the presence of a solvent, or

-   γ) when phenylacetic acids of the formula (XXVII-b)

-   -   in which    -   X and Z are each as defined above    -   are reacted with halogen compounds of the formula (XXXIII),        Y-Hal  (XXXIII)    -   in which    -   Y is as defined above and    -   Hal represents chlorine, bromine or iodine    -   in the presence of a solvent, a base and a catalyst (preferably        one of the abovementioned palladium complexes).

The compounds of the formulae (XII) and (XXXIII) are known, some of themare commercially available, or they can be prepared by processes knownin principle. Some of the phenylacetic acids of the formula (XXVII-a)are known from WO 96/35 664 and WO 97/02243, or they can be prepared bythe processes described therein.

The compounds of the formula (XXVII-b) and (XXII) are novel.

The compounds of the formula (XXVII-b)

in which

-   X and Z are each as defined above-   are obtained, for example, when phenylacetic acids of the formula    (XXVII-a)

in which

-   X, Y′ and Z are each as defined above-   are reacted with lithium compounds of the formula (XXXIV)    Li—R²¹  (XXXIV)    in which-   R²¹ represents C₁–C₈-alkyl or phenyl, preferably represents n-C₄H₉,    and boronic esters of the formula (XXXV)    B(OR⁸)₃  (XXXV)    in which-   R⁸ is as defined above-   in the presence of a diluent.

The compounds of the formulae (XXXIV) and (XXXV) are commerciallyavailable compounds.

The compounds of the formula (XXXII)

in which

-   X. Y, Z and R⁸ are each as defined above-   are obtained, for example,-   when phenylacetic esters of the formula (XXII-a)

in which

-   R⁸, X, Y′ and Z are each as defined above-   are reacted with boronic acids of the formula (XII)

in which

-   Y is as defined above-   in the presence of a solvent, a base and a catalyst (preferably one    of the abovementioned palladium complexes).

Some of the phenylacetic esters of the formula (XXXII-a) are known fromthe applications WO 96/35 664 and WO 97/02 243, or they can be preparedby the processes described therein.

The compounds of the formula (IV)

in which

-   A, B, W, X, Y, Z and R⁸ are each as defined above-   required as starting materials in the above process (C) are novel.

They can be prepared by methods known in principle.

The compounds of the formula (IV) are obtained, for example, whensubstituted phenylacetic esters of the formula (XXXII)

in which

X, Y, R⁸ and Z are each as defined above are acylated with2-benzylthio-carbonyl halides of the formula (XXXVI)

in which

-   A, B and W are each as defined above and-   Hal represents halogen (in particular chlorine or bromine)    in the presence of strong bases (see, for example, M. S.    Chambers, E. J. Thomas, D. J. Williams, J. Chem. Soc. Chem. Commun.,    (1987), 1228).

The compounds of the formula (XXXII) are novel. Compounds of the formula(XXXII) are obtained, for example, when compounds of the formula (XXVII)

in which

-   X, Y and Z are each as defined above-   are esterified in the presence of alcohols and dehydrating agents    (for example conc. sulphuric acid), or when alcohols are acylated    with compounds of the formula (XXIV)

in which

-   X, Y, Z and Hal are each as defined above    (Chem. Reviews 52, 237–416 (1953)).

Some of the benzylthio-carbonyl halides of the formula (XXXVI) areknown, and/or they can be prepared by known processes (J. Antibiotics(1983), 26, 1589).

The halogenocarbonyl ketenes of the formula (V) required as startingmaterials in the above processes (D), (E) and (F) are novel. They can beprepared by methods which are generally known in principle (cf., forexample, Org. Prep. Proced. Int., 7, (4), 155–158, 1975 and DE 1 945703). Thus, for example, the compounds of the formula (V)

in which

-   X, Y and Z are each as defined above and-   Hal represents chlorine or bromine are obtained when substituted    phenylmalonic acids of the formula (XXXVII)

in which

-   X, Y and Z are each as defined above-   are reacted with acyl halides, such as, for example, thionyl    chloride, phosphorus(V) chloride, phosphorus(III) chloride, oxalyl    chloride, phosgene or thionyl bromide, if appropriate in the    presence of catalysts, such as, for example, dimethylformamide,    methyl-steryl-formamide or triphenylphosphine and if appropriate in    the presence of bases such as, for example, pyridine or    triethylamine.

The substituted phenylmalonic acids of the formula (XXXVII) are novel.They can be prepared by generally known processes (cf., for example,Organikum, VEB Deutscher Verlag der Wissenschaften, Berlin 1977, p. 517ff, EP-A-528 156, WO 96/35 664, WO 97/02 243).

Thus, phenylmalonic acids of the formula (XXXVII)

in which

-   X, Y and Z are each as defined above-   are obtained when phenylmalonic esters of the formula (VI)

in which

-   X, Y, Z and R⁸ are each as defined above    are initially hydrolysed in the presence of a base and in a solvent    and subsequently carefully acidified (EP-528 156, WO 96/35 664, WO    97/02 243).

The malonic esters of the formula (VI)

in which

-   X, Y, Z and R⁸ are each as defined above-   are novel.

They can be prepared by generally known methods of organic chemistry(cf., for example, Tetrahedron Lett. 27, 2763 (1986) and Organikum, VEBDeutscher Verlag der Wissenschaften, Berlin 1977, p. 587 ff.).

Some of the hydrazines of the formula (VII)A-NH—NH-D  (VII),in which

-   A and D are each as defined above    required as starting materials for the process (D) according to the    invention are known, and/or they can be prepared by methods known    from the literature (cf., for example, Liebigs Ann. Chem. 585, 6    (1954); Reaktionen der organischen Synthese, C. Ferri, p. 212, 513;    Georg Thieme Verlag Stuttgart, 1978; Liebigs Ann. Chem. 443, 242    (1925); Chem. Ber. 98, 2551 (1965), EP-508 126).

The carbonyl compounds of the formula (VIII)

in which

-   A and D are each as defined above-   or their silyl enol ethers of the formula (VIIIa)

in which

-   A, D and R⁸ are each as defined above-   required as starting materials for the process (E) according to the    invention are commercially available, generally known compounds or    compounds which are obtainable by known processes.

The preparation of the ketene acid chlorides of the formula (V),required as starting materials for carrying out the process (F)according to the invention has already been described above. Thethioamides of the formula (IX)

in which

-   A is as defined above-   required for carrying out the process (F) according to the invention    are compounds which are generally known in organic chemistry.

The compounds of the formula (X)

in which

-   A, B, Q¹, Q², X, Y, Z and R⁸ are each as defined above-   required as starting materials in the above process (G) are novel.

They can be prepared by methods known in principle.

The 5-aryl-4-ketocarboxylic esters of the formula (X) are obtained, forexample, when 5-aryl-4-ketocarboxylic acids of the formula (XXXVIII)

in which

-   X, Y, Z, A, B, Q¹ and Q² are each as defined above-   are esterified (cf., for example, Organikum, 15th edition, Berlin,    1977, page 499) or alkylated (see Preparation Example).

The 5-aryl-4-ketocarboxylic acids of the formula (XXXVIII)

in which

-   A, B, Q¹, Q², X, Y and Z are each as defined above    are novel but can be prepared by methods known in principle (see    Preparation Example).

The 5-aryl-4-ketocarboxylic acids of the formula (XXXVIII) are obtained,for example, when 2-phenyl-3-oxo-adipic esters of the formula (XXXIX)

in which

-   A, B, D¹, D², X, Y and Z are each as defined above and-   R⁸ and R^(8′) each represent alkyl (in particular C₁–C₈-alkyl)    are decarboxylated, if appropriate in the presence of a diluent and    if appropriate in the presence of a base or acid (cf., for example,    Organikum, 15th edition, Berlin, 1977, pages 519 to 521).

The compounds of the formula (XXXIX)

in which

-   A, B, Q¹, Q², X, Y, Z, R⁸, R⁸′ are each as defined above-   are novel.

The compounds of the formula (XXXIX) are obtained, for example, whendicarboxylic monoester chlorides of the formula (XL),

in which

-   A, B, Q¹, Q² and R⁸ are each as defined above and-   Hal represents chlorine or bromine-   or carboxylic anhydrides of the formula (XLI)

in which

-   A, B, Q¹ and Q² are each as defined above-   are acylated with a phenyl acetic ester of the formula (XXII)

in which

-   X, Y, Z and R^(8′) are each as defined above    in the presence of a diluent and in the presence of a base (cf., for    example, M. S. Chambers, E. J. Thomas, D. J. Williams, J. Chem. Soc.    Chem. Commun., (1987), 1228, cf. also the Preparation Examples).

Some of the compounds of the formulae (XL) and (XLI) are known compoundsof organic chemistry, and/or they can be prepared in a simple manner bymethods known in principle.

The compounds of the formula (XI)

in which

-   A, B, Q³, Q⁴, Q⁵, Q⁶, X, Y, Z and R⁸ are each as defined above-   required as starting materials in the above process (H) are novel.

They can be prepared by methods known in principle.

The 6-aryl-5-ketocarboxylic esters of the formula (XI) are obtained, forexample, when 6-aryl-5-ketocarboxylic acids of the formula (XLII)

in which

-   A, B, Q³, Q⁴, Q⁵, Q⁶, X, Y and Z are each as defined above    are esterified (cf., for example, Organikum, 15th edition, Berlin,    1977, page 499 and Preparation Example).

The 6-aryl-5-ketocarboxylic acids of the formula (XLII)

in which

-   A, B, Q³, Q⁴, Q⁵, Q⁶, X, Y and Z are each as defined above    are novel. They can be prepared by methods known in principle, for    example by hydrolysing and decarboxylating

substituted 2-phenyl-3-oxo-heptanedioic esters of the formula (XLIII)

in which

-   A, B, Q³, Q⁴, Q⁵, Q⁶, X, Y and Z are each as defined above and-   R⁸ and R^(8′) are each alkyl (preferably C₁–C₆-alkyl),    if appropriate in the presence of a diluent and if appropriate in    the presence of a base or acid (cf., for example, Organikun, 15th    edition, Berlin, 1977, page 519 to 521 and Preparation Example).

The compounds of the formula (XLIII)

in which

-   A, B, Q³, Q⁴, Q⁵, Q⁶, X, Y, Z, R⁸ and R^(8′) are each as defined    above    are novel. They can be obtained

when dicarboxylic anhydrides of the formula (XLIV),

in which

-   A, B, Q³, Q⁴, Q⁵ and Q⁶ are each as defined above-   are condensed with a substituted phenylacetic ester of the formula    (XXXII)

in which

-   X, Y, Z and R^(8′) are each as defined above-   in the presence of a diluent and in the presence of a base.

Some of the compounds of the formula (XLIV) are known, and/or they canbe prepared by known processes.

The compounds of the formula (XXXII) have already been described underthe precursors for the process (B). Furthermore, compounds of theformula (XXXII) are obtained by reacting substituted1,1,1-trichloro-2-phenylethanes of the formula (XLV)

in which

-   X, Y and Z are each as defined above initially with alkoxides (for    example alkali metal alkoxides such as sodium methoxide or sodium    ethoxide) in the presence of a diluent (for example the alcohol    derived from the alkoxide) at temperatures between 0° C. and 150°    C., preferably between 20° C. and 120° C., and subsequently with an    acid (preferably an inorganic acid such as, for example, sulphuric    acid) at temperatures between −20° C. and 150° C., preferably    between 0° C. and 100° C. (cf. DE 3 314 249).

The compounds of the formula (XLV) are novel, they can be prepared byprocesses known in principle.

The compounds of the formula (XLV) are obtained, for example, whenanilines of the formula (XLVI)

in which

-   X, Y and Z are each as defined above-   are reacted with vinylidene chloride (CH₂═CCl₂) in the presence of    an alkyl nitrite of the formula (XLVII)    R²¹—ONO  (XLVII)-   in which-   R²¹ represents alkyl, preferably C₁–C₆-alkyl, in the presence of    copper(II) chloride and, if appropriate, in the presence of a    diluent (for example an aliphatic nitrile such as acetonitrile), at    a temperature of from −20° C. to 80° C., preferably from 0° C. to    60° C.

The compounds of the formula (XLVII) are known compounds of organicchemistry. Copper(II) chloride and vinylidene chloride have been knownfor a long time and are commercially available.

The compounds of the formula (XLVI) are novel.

Compounds of the formula (XLVI)

in which

-   X, Y and Z are each as defined above,-   for example, are obtained when anilines of the formula (XLVI-a)

in which

-   X and Z are each as defined above-   Y′ represents halogen (preferably represents bromine)-   are reacted with boronic acids of the formula (XII)

in which

-   Y is as defined above-   in the presence of a solvent, a base and a catalyst (preferably a    palladium complex, such as, for example,    tetrakis(tripheylphosphine)palladium.

Some of the compounds of the formulae (I-1′-a) to (I-8′-a) in which A,B, D, Q¹, Q², Q³, Q⁴, Q⁵, Q⁶, X and Z are each as defined above and Y′represents chlorine and bromine, preferably represents bromine, andwhich are required as starting materials in the above process (I) areknown (WO 96/35 664, WO 97/02 243) or they can be prepared by theprocesses described therein or by processes (A) to (H).

Some of the boronic acids of the formula (XII)

in which

-   Y is as defined above    are commercially available, or they can be prepared in a simple    manner by generally known processes.

The acyl halides of the formula (XIII), carboxylic anhydrides of theformula (XIV), chloroformic esters or chloroformic thioesters of theformula (XV), chloromonothioformic esters or chlorodithioformic estersof the formula (XVI), sulphonyl chlorides of the formula (XVII),phosphorus compounds of the formula (XVIII) and metal hydroxides, metalalkoxides or amines of the formulae (XIX) and (XX) and isocyanates ofthe formula (XXI) and carbamoyl chlorides of the formula (XXII)furthermore required as starting materials for carrying out theprocesses (J), (K), (L), (M), (N), (O) and (P) according to theinvention are generally known compounds of organic or inorganicchemistry.

Moreover, the compounds of the formulae (VII), (VIII), (IX), (XIII) to(XXIII), (XXVI), (XXVIII), (XXX), (XXXVI), (XL), (XLI) and (XLVI-a) areknown from the patent applications cited at the outset, and/or they canbe prepared by the methods given therein.

The process (A) is characterized in that compounds of the formula (II)in which A, B, D, X, Y, Z and R⁸ are each as defined above are subjectedto an intramolecular condensation in the presence of a base.

Suitable diluents for the process (A) according to the invention are allinert organic solvents. Preference is given to using hydrocarbons, suchas toluene and xylene, furthermore ethers, such as dibutyl ether,tetrahydrofuran, dioxane, glycol dimethyl ether and diglycol dimethylether, moreover polar solvents, such as dimethyl sulphoxide, sulpholane,dimethylformamide and N-methyl-pyrrolidone, and also alcohols, such asmethanol, ethanol, propanol, iso-propanol, butanol, iso-butanol andtert-butanol.

Suitable bases (deprotonating agents) for carrying out the process (A)according to the invention are all customary proton acceptors.Preference is given to using alkali metal and alkaline earth metaloxides, hydroxides and carbonates, such as sodium hydroxide, potassiumhydroxide, magnesium oxide, calcium oxide, sodium carbonate, potassiumcarbonate and calcium carbonate, which can also be employed in thepresence of phase-transfer catalysts, such as, for example,triethylbenzylammonium chloride, tetrabutylammonium bromide, Adogen 464(=methyltrialkyl(C₈–C₁₀)ammonium chloride) or TDA 1(=tris-(methoxyethoxyethyl)-amine). Alkali metals such as sodium andpotassium can also be used. Furthermore, alkali metal and alkaline earthmetal amides and hydrides, such as sodium amide, sodium hydride andcalcium hydride, and additionally also alkali metal alkoxides, such assodium methoxide, sodium ethoxide and potassium tert-butoxide can beemployed.

When carrying out the process (A) according to the invention, thereaction temperatures can be varied within a relatively wide range. Ingeneral, the reaction is carried out at temperatures between 0° C. and250° C., preferably between 50° C. and 150° C.

The process (A) according to the invention is generally carried outunder atmospheric pressure.

When carrying out process (A) according to the invention, the reactioncomponents of the formula (II) and the deprotonating bases are generallyemployed in approximately double-equimolar amounts. However, it is alsopossible to use a larger excess (up to 3 mol) of one component or theother.

The process (B) is characterized in that compounds of the formula (III)in which A, B, X, Y, Z and R⁸ are each as defined above are subjected toan intramolecular condensation in the presence of a diluent and in thepresence of a base.

Suitable diluents for the process (B) according to the invention are allinert organic solvents. Preference is given to using hydrocarbons, suchas toluene and xylene, furthermore ethers, such as dibutyl ether,tetrahydrofuran, dioxane, glycol dimethyl ether and diglycol dimethylether, moreover polar solvents, such as dimethyl sulphoxide, sulpholane,dimethylformamide and N-methyl-pyrrolidone, and also alcohols, such asmethanol, ethanol, propanol, iso-propanol, butanol, iso-butanol andtert-butanol.

Suitable bases (deprotonating agents) for carrying out the process (B)according to the invention are all customary proton acceptors.Preference is given to using alkali metal and alkaline earth metaloxides, hydroxides and carbonates, such as sodium hydroxide, potassiumhydroxide, magnesium oxide, calcium oxide, sodium carbonate, potassiumcarbonate and calcium carbonate, which can also be employed in thepresence of phase-transfer catalysts, such as, for example,triethylbenzylammonium chloride, tetrabutylammonium bromide, Adogen 464(=methyltrialkyl(C₈–C₁₀)ammonium chloride) or TDA 1(=tris-(methoxyethoxyethyl)-amine). Alkali metals such as sodium andpotassium can also be used. Furthermore, alkali metal and alkaline earthmetal amides and hydrides, such as sodium amide, sodium hydride andcalcium hydride, and additionally also alkali metal alkoxides, such assodium methoxide, sodium ethoxide and potassium tert-butoxide can beemployed.

When carrying out the process (B) according to the invention, thereaction temperatures can be varied within a relatively wide range. Ingeneral, the reaction is carried out at temperatures between 0° C. and250° C., preferably between 50° C. and 150° C.

The process (B) according to the invention is generally carried outunder atmospheric pressure.

When carrying out the process (B) according to the invention, thereaction components of the formula (III) and the deprotonating bases aregenerally employed in approximately equimolar amounts. However, it isalso possible to use a relatively large excess (up to 3 mol) of onecomponent or the other.

The process (C) is characterized in that compounds of the formula (IV)in which A, B, W, X, Y, Z and R⁸ are each as defined above are cyclizedintramolecularly in the presence of an acid and, if appropriate, in thepresence of a diluent.

Suitable diluents for the process (C) according to the invention are allinert organic solvents. Preference is given to using hydrocarbons, suchas toluene and xylene, furthermore halogenated hydrocarbons such asdichloromethane, chloroform, ethylene chloride, chlorobenzene,dichlorobenzene, moreover polar solvents, such as dimethyl sulphoxide,sulpholane, dimethyl formamide and N-methyl-pyrrolidone. Furthermore, itis possible to employ alcohols such as methanol, ethanol, propanol,iso-propanol, butanol, isobutanol, tert-butanol.

If appropriate, the acid used can also serve as diluent.

Suitable acids for the process (C) according to the invention are allcustomary inorganic and organic acids, such as, for example, hydrohalicacids, sulphuric acid, alkyl, aryl and haloalkylsulphonic acids, inparticular halogenated alkylcarboxylic acids, such as, for example,trifluoroacetic acid.

When carrying out the process (C) according to the invention, thereaction temperatures can be varied within a relatively wide range. Ingeneral, the reaction is carried out at temperatures between 0° C. and250° C., preferably between 50° C. and 150° C.

The process (C) according to the invention is generally carried outunder atmospheric pressure.

When carrying out the process (C) according to the invention, thereaction components of the formula (IV) and the acid are employed, forexample, in equimolar amounts. However, it is also possible, ifappropriate, to use the acid as solvent or as catalyst.

The processes (D-α) and (D-β) are characterized in that compounds of theformula (V) or (VI) in which X, Y, Z, R⁸ and Hal are each as definedabove are reacted with compounds of the formula (VII) in which A and Dare each as defined above, if appropriate in the presence of a base andif appropriate in the presence of a diluent.

Suitable diluents for the processes (D-α) and (D-β) according to theinvention are all inert organic solvents. Preference is given to usinghydrocarbons, such as toluene and xylene, furthermore ethers, such asdibutyl ether, tetrahydrofuran, dioxane, glycol dimethyl ether anddiglycol dimethyl ether, moreover polar solvents, such as dimethylsulphoxide, sulpholane, dimethylformamide and N-methyl-pyrrolidone, andalso, only in the case where compounds of the formula (VI) are employed,alcohols such as methanol, ethanol, propanol, iso-propanol, butanol,iso-butanol and tert-butanol.

When compounds of the formula (V) are employed, suitable bases areinorganic bases, in particular alkali metal or alkaline earth metalcarbonates such as sodium carbonate, potassium carbonate or calciumcarbonate, and also organic bases, such as, for example, pyridine ortriethylamine, and when compounds of the formula (VI) are employed,alkali metal and alkaline earth metal oxides, hydroxides and carbonates,such as sodium hydroxide, potassium hydroxide, magnesium hydroxide,calcium oxide, sodium carbonate, potassium carbonate and calciumcarbonate, which can also be employed in the presence of phase-transfercatalysts, such as, for example, triethylbenzylammonium chloride,tetrabutylammonium bromide, Adogen 464 (=methyltrialkyl(C₈–C₁₀)-ammoniumchloride) or TDA 1 (=tris-(methoxyethoxyethyl)-amine), furthermorealkali metals, such as sodium or potassium, alkali metal amides andhydrides and alkaline earth metal amides and hydrides, such as sodiumamide, sodium hydride and calcium hydride, and additionally alkali metalalkoxides, such as sodium methoxide and potassium tert-butoxide.

When carrying out the processes (D-α) and (D-β) according to theinvention, the reaction temperatures can be varied within a relativelywide range. In general, the reaction is carried out at temperaturesbetween −20° C. and 250° C., preferably between 0° C. and 150° C.

The processes (D-α) and (D-β) according to the invention are generallycarried out under atmospheric pressure.

When carrying out the processes (D-α) and (D-β) according to theinvention, the reaction components of the formulae (V) and (VII) or (VI)and (VII) and the deprotonating bases which are employed if appropriateare generally employed in approximately equimolar amounts. However, itis also possible to use a relatively large excess (up to 3 mol) of onecomponent or the other.

The process (E) according to the invention is characterized in thatcarbonyl compounds of the formula (VIII) or enol ethers thereof of theformula (VIII-a) are reacted with ketene acid halides of the formula (V)in the presence of a diluent and, if appropriate, in the presence of anacid acceptor.

Suitable diluents for the process (E) according to the invention are allinert organic solvents. Preference is given to using hydrocarbons, suchas toluene and xylene, furthermore ethers, such as dibutyl ether, glycoldimethyl ether and diglycol dimethyl ether, moreover polar solvents,such as dimethyl sulphoxide, sulpholane, dimethylformamide orN-methyl-pyrrolidone.

Suitable acid acceptors for carrying out the process variant E)according to the invention are all customary acid acceptors.

Preference is given to using tertiary amines, such as triethylamine,pyridine, diazabicyclooctane (DABCO), diazabicycloundecane (DBU),diazabicyclononene (DBN), Hünig base and N,N-dimethyl-aniline.

When carrying out the process variant E) according to the invention, thereaction temperatures can be varied within a relatively wide range.Advantageously, the reaction is carried out at temperatures between 0°C. and 250° C., preferably between 50° C. and 220° C.

The process (E) according to the invention is advantageously carried outunder atmospheric pressure.

When carrying out the process (E) according to the invention, thereaction components of the formulae (VIII) and (V) in which A, D, X, Yand Z are each as defined above and Hal represents halogen, and, ifappropriate, the acid acceptors, are generally employed in approximatelyequimolar amounts. However, it is also possible to use a relativelylarge excess (up to 5 mol) of one component or the other.

The process (F) according to the invention is characterized in thatthioamides of the formula (IX) are reacted with ketene acid halides ofthe formula (V) in the presence of a diluent and, if appropriate, in thepresence of an acid acceptor.

Suitable diluents for the process variant F) according to the inventionare all inert organic solvents. Preference is given to usinghydrocarbons, such as toluene and xylene, furthermore ethers, such asdibutyl ether, glycol dimethyl ether and diglycol dimethyl ether,moreover polar solvents, such as dimethyl sulphoxide, sulpholane,dimethylformamide and N-methyl-pyrrolidone.

Suitable acid acceptors for carrying out the process (F) according tothe invention are all customary acid acceptors.

Preference is given to using tertiary amines, such as triethylamine,pyridine, diazabicyclooctane (DABCO), diazabicycloundecane (DBU),diazabicyclononene (DBN), Hünig base and N,N-dimethyl-aniline.

When carrying out the process (F) according to the invention, thereaction temperatures can be varied within a relatively wide range.Advantageously, the reaction is carried out at temperatures between 0°C. and 250° C., preferably between 20° C. and 220° C.

The process (F) according to the invention is advantageously carried outunder atmospheric pressure.

When carrying out the process (F) according to the invention, thereaction components of the formulae (IX) and (V) in which A, X, Y and Zare each as defined above and Hal represents halogen, and, ifappropriate, the acid acceptors, are generally employed in approximatelyequimolar amounts. However, it is also possible to use a relativelylarge excess (up to 5 mol) of one component or the other.

The process (G) is characterized in that compounds of the formula (X) inwhich A, B, Q¹, Q², Y, Z and R⁸ are each as defined above are subjectedto an intramolecular condensation in the presence of a base.

Suitable diluents for the process (G) according to the invention are allorganic solvents which are inert towards the reaction participants.Preference is given to using hydrocarbons, such as toluene and xylene,furthermore ethers, such as dibutyl ether, tetrahydrofuran, dioxane,glycol dimethyl ether and diglycol dimethyl ether, moreover polarsolvents, such as dimethyl sulphoxide, sulpholane, dimethylformamide andN-methyl-pyrrolidone. It is furthermore possible to use alcohols, suchas methanol, ethanol, propanol, iso-propanol, butanol, isobutanol,tert-butanol.

Suitable bases (deprotonating agents) for carrying out the process (G)according to the invention are all customary proton acceptors.Preference is given to using alkali metal and alkaline earth metaloxides, hydroxides and carbonates, such as sodium hydroxide, potassiumhydroxide, magnesium oxide, calcium oxide, sodium carbonate, potassiumcarbonate and calcium carbonate, which can also be employed in thepresence of phase-transfer catalysts, such as, for example,triethylbenzylammonium chloride, tetrabutylammonium bromide, Adogen 464(methyltrialkyl(C₈–C₁₀)ammonium chloride) or TDA 1(tris-(methoxyethoxyethyl)amine). Alkali metals such as sodium orpotassium can also be used. Furthermore, alkali metal and alkaline earthmetal amides and hydrides, such as sodium amide, sodium hydride andcalcium hydride, and additionally also alkali metal alkoxides, such assodium methoxide, sodium ethoxide and potassium tert-butoxide can beemployed.

When carrying the process (G) according to the invention, the reactiontemperatures can be varied within a relatively wide range. In general,the reaction is carried out at temperatures between −75° C. and 250° C.,preferably between −50° C. and 150° C.

The process (G) according to the invention is generally carried outunder atmospheric pressure.

When carrying out the process (G) according to the invention, thereaction components of the formula (X) and the deprotonating bases aregenerally employed in approximately equimolar amounts. However, it isalso possible to use a relatively large excess (up to 3 mol) of onecomponent or the other.

The process (H) is characterized in that compounds of the formula (XI)in which A, B, Q³, Q⁴, Q⁵, Q⁶, X, Y, Z and R⁸ are each as defined aboveare subjected to an intramolecular condensation in the presence ofbases.

Suitable diluents for the process (H) according to the invention are allorganic solvents which are inert towards the reaction participants.Preference is given to using hydrocarbons, such as toluene and xylene,furthermore ethers, such as dibutyl ether, tetrahydrofuran, dioxane,glycol dimethyl ether and diglycol dimethyl ether, moreover polarsolvents, such as dimethyl sulphoxide, sulpholane, dimethylformamide andN-methyl-pyrrolidone. Alcohols, such as methanol, ethanol, propanol,iso-propanol, butanol, isobutanol and tert-butanol can also be used.

Suitable bases (deprotonating agents) for carrying out the process (H)according to the invention are all customary proton acceptors.Preference is given to using alkali metal and alkaline earth metaloxides, hydroxides and carbonates, such as sodium hydroxide, potassiumhydroxide, magnesium oxide, calcium oxide, sodium carbonate, potassiumcarbonate and calcium carbonate, which can also be employed in thepresence of phase-transfer catalysts, such as, for example,triethylbenzylammonium chloride, tetrabutylammonium bromide, Adogen 464(methyltrialkyl(C₈–C₁₀)ammonium chloride) or TDA 1(tris-(methoxyethoxyethyl)amine). Alkali metals such as sodium andpotassium can also be used. Furthermore, alkali metal and alkaline earthmetal amides and hydrides, such as sodium amide, sodium hydride andcalcium hydride, and additionally also alkali metal alkoxides, such assodium methoxide, sodium ethoxide and potassium tert-butoxide can beemployed.

When carrying the process (H) according to the invention, the reactiontemperatures can be varied within a relatively wide range. In general,the reaction is carried out at temperatures between 0° C. and 250° C.,preferably between 50° C. and 150° C.

The process (H) according to the invention is generally carried outunder atmospheric pressure.

When carrying out the process (H) according to the invention, thereaction components of the formula (XII) and the deprotonating bases aregenerally employed in approximately equimolar amounts. However, it isalso possible to use a relatively large excess (up to 3 mol) of onecomponent or the other.

For carrying out the process (I) according to the invention,palladium(0) complexes are suitable as catalysts. Use is made, forexample, of tetrakis(triphenylphosphine)palladium. Also suitable arepalladium(II) compounds such as bis(triphenylphosphine)palladium(II)chloride.

Suitable acid acceptors for carrying out the process (I) according tothe invention are inorganic or organic bases. These preferably includealkaline earth metal or alkali metal hydroxides, acetates, carbonates orbicarbonates, such as, for example, sodium hydroxide, potassiumhydroxide, barium hydroxide or ammonium hydroxide, sodium acetate,potassium acetate, calcium acetate or ammonium acetate, sodiumcarbonate, potassium carbonate or ammonium carbonate, sodium bicarbonateor potassium bicarbonate, alkali metal fluorides, such as, for example,potassium fluoride, caesium fluoride, and also tertiary amines, such astrimethylamine, triethylamine, tributylamine, N,N-dimethylaniline,N,N-dimethylbenzylamine, pyridine, N-methylpiperidine,N-methylmorpholine, N,N-dimethylaminopyridine, diazabicyclooctane(DABCO), diazabicyclononene (DBN) or diazabicycloundecene (DBU).

Suitable diluents for carrying out the process (I) according to theinvention are water, organic solvents and any mixtures thereof. Examplesinclude: aliphatic, alicyclic or aromatic hydrocarbons, such as, forexample, petroleum ether, hexane, heptane, cyclohexane,methylcyclohexane, benzene, toluene, xylene or decalin; halogenatedhydrocarbons, such as, for example, chlorobenzene, dichlorobenzene,methylene chloride, chloroform, carbon tetrachloride, dichloroethane,trichloroethane or tetrachloroethylene; ethers, such as diethyl ether,diisopropyl ether, methyl t-butyl ether, methyl t-amyl ether, dioxane,tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane, diethyleneglycol dimethyl ether or anisole; alcohols, such as methanol, ethanol,n- or i-propanol, n-, iso-, sec- or tert-butanol, ethanediol,propane-1,2-diol, ethoxyethanol, methoxyethanol, diethylene glycolmonomethyl ether, diethylene glycol monoethyl ether; water.

The reaction temperature in the process (I) according to the inventioncan be varied within a relatively wide range. In general, the reactionis carried out at temperatures between 0° C. and +140° C., preferablybetween 50° C. and +100° C.

When carrying out the process (I) according to the invention, boronicacid of the formula (XII) and compounds of the formulae (I-1-a) to(I-8-a) are employed in a molar ratio of from 1:1 to 3:1, preferablyfrom 1:1 to 2:1. In general, 0.005 to 0.5 mol, preferably 0.01 mol to0.1 mol of catalyst is employed per mole of the compounds of theformulae (I-1-a) to (I-8-a). The base is usually employed in excess.

The process (J-α) is characterized in that compounds of the formulae(I-1-a) to (I-8-a) are in each case reacted with carbonyl halides of theformula (XIII), if appropriate in the presence of a diluent and ifappropriate in the prescence of an acid binder.

Suitable diluents for the process (J-α) according to the invention areall solvents which are inert towards the acyl halides. Preference isgiven to using hydrocarbons, such as benzine, benzene, toluene, xyleneand tetralin, furthermore halogenated hydrocarbons, such as methylenechloride, chloroform, carbon tetrachloride, chlorobenzene ando-dichlorobenzene, moreover ketones, such as acetone and methylisopropyl ketone, furthermore ethers, such as diethyl ether,tetrahydrofuran and dioxane, additionally carboxylic esters, such asethyl acetate, and also strongly polar solvents, such as dimethylsulphoxide and sulpholane. The hydrolytic stability of the acyl halidepermitting, the reaction can also be carried out in the presence ofwater.

Suitable acid binders for the reaction according to the process (J-α)according to the invention are all customary acid acceptors. Preferenceis given to using tertiary amines, such as triethylamine, pyridine,diazabicyclooctane (DABCO), diazabicyclo-undecene (DBU),diazabicyclononene (DBN), Hünig base and N,N-dimethyl-aniline,furthermore alkaline earth metal oxides, such as magnesium oxide andcalcium oxide, moreover alkali metal and alkaline earth metalcarbonates, such as sodium carbonate, potassium carbonate and calciumcarbonate, and also alkali metal hydroxides such as sodium hydroxide andpotassium hydroxide.

The reaction temperatures in the process (J-α) according to theinvention can be varied within a relatively wide range. In general, thereaction is carried out at temperatures between −20° C. and +150° C.,preferably between 0° C. and 100° C.

When carrying out the process (J-α) according to the invention, thestarting materials of the formulae (I-1-a) to (I-8-a) and the carbonylhalide of the formula (XIII) are generally in each case employed inapproximately equivalent amounts. However, it is also possible to employa relatively large excess (up to 5 mol) of the carbonyl halide. Work-upis carried out by customary methods.

The process (J-β) is characterized in that compounds of the formulae(I-1-a) to (I-8-a) are reacted with carboxylic anhydrides of the formula(XIV), if appropriate in the presence of a diluent and if appropriate inthe presence of an acid binder.

Preferred diluents for the process (J-β) according to the invention arethose diluents which are also preferred when acyl halides are used.Otherwise, it is also possible for a carboxylic anhydride employed inexcess to act simultaneously as a diluent.

In the process (J-β), acid binders which are added, if appropriate, arepreferably those acid binders which are also preferred when acyl halidesare used.

In the process (J-β) according to the invention, the reactiontemperatures can be varied within a relatively wide range. In general,the reaction is carried out at temperatures between −20° C. and +150°C., preferably between 0° C. and 100° C.

When carrying out the process (J-β) according to the invention, thestarting materials of the formulae (I-1-a) to (I-8-a) and the carboxylicanhydride of the formula (XIV) are generally each employed inapproximately equivalent amounts. However, it is also possible to use arelatively large excess (up to 5 mol) of the carboxylic anhydride.Work-up is carried out by customary methods.

In general, the adopted procedure is to remove diluent and excesscarboxylic anhydride and also the carboxylic acid formed by distillationor by washing with an organic solvent or with water.

The process (K) is characterized in that compounds of the formulae(I-1-a) to (I-8-a) are in each case reacted with chloroformic esters orchloroformic thiol esters of the formula (XV), if appropriate in thepresence of a diluent and if appropriate in the presence of an acidbinder.

Suitable diluents for the reaction according to the process (K)according to the invention are all customary acid acceptors. Preferenceis given to using tertiary amines, such as triethylamine, pyridine,DABCO, DBU, DBA, Hünig base and N,N-dimethyl-aniline, furthermorealkaline earth metal oxides, such as magnesium oxide and calcium oxide,moreover alkali metal carbonates and alkaline earth metal carbonates,such as sodium carbonate, potassium carbonate and calcium carbonate, andalso alkali metal hydroxides such as sodium hydroxide and potassiumhydroxide.

Suitable diluents for the process (K) according to the invention are allsolvents which are inert towards the chloroformic esters or chloroformicthiol esters. Preference is given to using hydrocarbons, such asbenzine, benzene, toluene, xylene and tetralin, furthermore halogenatedhydrocarbons, such as methylene chloride, chloroform, carbontetrachloride, chlorobenzene and o-dichlorobenzene, moreover ketones,such as acetone and methyl isopropyl ketone, furthermore ethers, such asdiethyl ether, tetrahydrofuran and dioxane, additionally carboxylicesters, such as ethyl acetate, and also strongly polar solvents, such asdimethyl sulphoxide and sulpholane.

When carrying out the process (K) according to the invention thereaction temperatures can be varied within a relatively wide range. Ifthe reaction is carried out in the presence of a diluent and an acidbinder, the reaction temperatures are generally between −20° C. and+100° C., preferably between 0° C. and 50° C.

The process (K) according to the invention is generally carried outunder atmospheric pressure.

When carrying out the process (K) according to the invention, thestarting materials of the formulae (I-1-a) to (I-8-a) and theappropriate chloroformic ester or chloroformic thiol ester of theformula (XV) are generally in each case employed in approximatelyequivalent amounts. However, it is also possible to employ a relativelylarge excess (up to 2 mol) of one component or the other. Work-up iscarried out by customary methods. In general, precipitated salts areremoved and the reaction mixture that remains is concentrated bystripping the diluent.

The process (L) according to the invention is characterized in thatcompounds of the formulae (I-1-a) to (I-8-a) are in each case reactedwith compounds of the formula (XVI) in the presence of a diluent and, ifappropriate, in the presence of an acid binder.

In the preparation process (L), approximately 1 mol ofchloromonothioformic ester or chlorodithioformic ester of the formula(XVI) is reacted per mole of starting material of the formulae (I-1-a)to (I-8-a), at from 0 to 120° C., preferably from 20 to 60° C.

Suitable diluents which are added if appropriate are all inert polarorganic solvents, such as ethers, amides, sulphones, sulphoxides, butalso halogenoalkanes.

Preference is given to using dimethyl sulphoxide, tetrahydrofuran,dimethylformamide or methylene chloride.

If, in a preferred embodiment, the enolate salt of the compounds (I-1-a)to (I-8-a) is prepared by addition of strong deprotonating agents, suchas, for example, sodium hydride or potassium tert-butoxide, it is notnecessary to add further acid binders.

If acid binders are employed, these are customary inorganic or organicbases, for example sodium hydroxide, sodium carbonate, potassiumcarbonate, pyridine, triethylamine.

The reaction can be carried out at atmospheric pressure or underelevated pressure and is preferably carried out at atmospheric pressure.Work-up is carried out by customary methods.

The process (M) according to the invention is characterized in thatcompounds of the formulae (I-1-a) to (I-8-a) are in each case reactedwith sulphonyl chlorides of the formula (XVII), if appropriate in thepresence of a diluent and if appropriate in the presence of an acidbinder.

In the preparation process (M), approximately 1 mol of sulphonylchloride of the formula (XVII) is reacted per mole of starting materialof the formula (I-1-a) to (I-8-a), at from −20 to 150° C., preferably atfrom 20 to 70° C. um.

Suitable diluents which are added if appropriate are all inert polarorganic solvents, such as ethers, amides, nitrites, sulphones,sulphoxides or halogenated hydrocarbons, such as methylene chloride.

Preference is given to using dimethyl sulphoxide, tetrahydrofuran,dimethylformamide, methylene chloride.

If, in a preferred embodiment, the enolate salt of the compounds (I-1-a)to (I-8-a) is prepared by addition of strong deprotonating agents (suchas, for example, sodium hydride or potassium tert-butoxide), it is notnecessary to add further acid binders.

If acid binders are employed, these are customary inorganic or organicbases, for example sodium hydroxide, sodium carbonate, potassiumcarbonate, pyridine, triethylamine.

The reaction can be carried out at atmospheric pressure or underelevated pressure and is preferably carried out at atmospheric pressure.Work-up is carried out by customary methods.

The process (N) according to the invention is characterized in thatcompounds of the formulae (I-1-a) to (I-8-a) are in each case reactedwith phosphorus compounds of the formula (XVIII), if appropriate in thepresence of a diluent and if appropriate in the presence of an acidbinder.

In the preparation process (N), 1 to 2, preferably 1 to 1.3, mol of thephosphorus compound of the formula (XVIII) are reacted per mole of thecompounds (I-1-a) to (I-8-a) at temperatures between 40° C. and 150° C.,preferably between −10 and 110° C., to give compounds of the formulae(I-1-e) to (I-8-e).

Suitable solvents which are added if appropriate are all inert polarorganic solvents, such as ethers, amides, nitrites, alcohols, sulphides,sulphones, sulphoxides, etc.

Preference is given to using acetonitrile, dimethyl sulphoxide,tetrahydrofuran, dimethylformamide, methylene chloride.

Suitable acid binders which are added if appropriate are customaryinorganic or organic bases such as hydroxides, carbonates or amines.Examples include sodium hydroxide, sodium carbonate, potassiumcarbonate, pyridine, triethylamine.

The reaction can be carried out at atmospheric pressure or underelevated pressure and is preferably carried out under atmosphericpressure. Work-up is carried out by customary methods of organicchemistry. The resulting end products are preferably purified bycrystallization, chromatographic purification or by so-called “incipientdistillation”, i.e. removal of the volatile components under reducedpressure.

The process (O) is characterized in that compounds of the formulae(I-1-a) to (I-8-a) are reacted with metal hydroxides or metal alkoxidesof the formula (XIX) or amines of the formula (XX), if appropriate inthe presence of a diluent.

Preferred diluents for the process (O) according to the invention areethers, such as tetrahydrofuran, dioxane, diethyl ether, or elsealcohols, such as methanol, ethanol, isopropanol, but also water.

The process (O) according to the invention is generally carried outunder atmospheric pressure.

The reaction temperatures are generally between −20° C. and 100° C.,preferably between 0° C. and 50° C.

The process (P) according to the invention is characterized in thatcompounds of the formulae (I-1-a) to (I-8-a) are in each case reactedwith (P-α) compounds of the formula (XXI), if appropriate in thepresence of a diluent and if appropriate in the presence of a catalyst,or (P-β) with compounds of the formula (XXII), if appropriate in thepresence of a diluent and if appropriate in the presence of an acidbinder.

In the preparation process (P-α), approximately one mol of isocyanate ofthe formula (XXI) is reacted per mole of starting material of theformulae (I-1-a) to (I-8-a), at from 0 to 100° C., preferably at from 20to 50° C.

Suitable diluents which are added if appropriate are all inert organicsolvents, such as ethers, amides, nitriles, sulphones, sulphoxides.

If appropriate, catalysts may be added to accelerate the reaction. Veryadvantageously, the catalysts which are employed are organotincompounds, such as, for example, dibutyltin dilaurate. The reaction ispreferably carried out at atmospheric pressure.

In the preparation process (P-β), approximately 1 mol of carbamoylchloride of the formula (XXII) is reacted per mole of starting materialof the formulae (I-1-a) to (I-8-a), at from −20 to 150° C., preferablyfrom 0 to 70° C. um.

Suitable diluents which are added if appropriate are all inert polarorganic solvents, such as ethers, amides, sulphones, sulphoxides orhalogenated hydrocarbons.

Preference is given to using dimethyl sulphoxide, tetrahydrofuran,dimethylformamide or methylene chloride.

If, in a preferred embodiment, the enolate salt of the compounds (I-1-a)to (I-8-a) is prepared by addition of strong deprotonating agents (suchas, for example, sodium hydride or potassium tert-butoxide), it is notnecessary to add further acid binders.

If acid binders are employed, these are customary inorganic or organicbases, for example sodium hydroxide, sodium carbonate, potassiumcarbonate, triethylamine or pyridine.

The reaction can be carried out at atmospheric pressure or underelevated pressure and is preferably carried out at atmospheric pressure.Work-up is carried out by customary methods.

The active compounds are suitable for controlling animal pests, inparticular insects, arachnids and nematodes, which are encountered inagriculture, in forestry, in the protection of stored products and ofmaterials, and in the hygiene sector, and have good plant tolerance andfavourable toxicity to warm-blooded animals. They may be preferablyemployed as plant protection agents. They are active against normallysensitive and resistant species and against all or some stages ofdevelopment. The abovementioned pests include:

From the order of the Isopoda, for example, Oniscus asellus,Armadillidium vulgare and Porcellio scaber.

From the order of the Diplopoda, for example, Blaniulus guttulatus.

From the order of the Chilopoda, for example, Geophilus carpophagus andScutigera spp.

From the order of the Symphyla, for example, Scutigerella immaculata.

From the order of the Thysanura, for example, Lepisma saccharina.

From the order of the Collembola, for example, Onychiurus armatus.

From the order of the Orthoptera, for example, Acheta domesticus,Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus spp. andSchistocerca gregaria.

From the order of the Blattaria, for example, Blatta orientalis,Periplaneta americana, Leucophaea maderae, Blattella germanica.

From the order of the Dermaptera, for example, Forficula auricularia.

From the order of the Isoptera, for example, Reticulitermes spp.

From the order of the Phthiraptera, for example, Pediculus humanuscorporis, Haematopinus spp., Linognathus spp., Trichodectes spp. andDamalinia spp.

From the order of the Thysanoptera, for example, Hercinothripsfemoralis, Thrips tabaci, Thrips palmi and Frankliniella accidentalis.

From the order of the Heteroptera, for example, Eurygaster spp.,Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodniusprolixus and Triatoma spp.

From the order of the Homoptera, for example, Aleurodes brassicae,Bemisia tabaci, Trialeurodes vaporariorunm, Aphis gossypii, Brevicorynebrassicae, Cryptomyzus ribis, Aphis fabae, Aphis pomi, Eriosomalanigerum, Hyalopterus arundinis, Phylloxera vastatrix, Pemphigus spp.,Macrosiphum avenae, Myzus spp., Phorodon humuli, Rhopalosiphum padi,Empoasca spp., Euscelis bilobatus, Nephotettix cincticeps, Lecaniumcorni, Saissetia oleae, Laodelphax striatellus, Nilaparvata lugens,Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp. and Psyllaspp.

From the order of the Lepidoptera, for example, Pectinophoragossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletisblancardella, Hyponomeuta padella, Plutella xylostella, Malacosomaneustria, Euproctis chrysorrhoea, Lymantria spp., Bucculatrixthurberiella, Phyllocnistis citrella, Agrotis spp., Euxoa spp., Feltiaspp., Earias insulana, Heliothis spp., Mamestra brassicae, Panolisflammea, Spodoptera spp., Trichoplusia ni, Carpocapsa pomonella, Pierisspp., Chilo spp., Pyrausta nubilalis, Ephestia kuehniella, Galleriamellonella, Tineola bisselliella, Tinea pellionella, Hofmannophilapseudospretella, Cacoecia podana, Capua reticulana, Choristoneurafumiferana, Clysia ambiguella, Homona magnanima, Tortrix viridana,Cnaphalocerus spp.

From the order of the Coleoptera, for example, Anobium punctatum,Rhizopertha dominica, Bruchidius obtectus, Acanthoscelides obtectus,Hylotrupes bajulus, Agelastica alni, Leptinotarsa decemlineata, Phaedoncochleariae, Diabrotica spp., Psylliodes chrysocephala, Epilachnavarivestis, Atomaria spp., Oryzaephilus surinamensis, Anthonomus spp.,Sitophilus spp., Otiorrhynchus sulcatus, Cosmopolites sordidus,Ceuthorrhynchus assimilis, Hypera postica, Dermestes spp., Trogodermaspp., Anthrenus spp., Attagenus spp., Lyctus spp., Meligethes aeneus,Ptinus spp., Niptus hololeucus, Gibbium psylloides, Tribolium spp.,Tenebrio molitor, Agriotes spp., Conoderus spp., Melolontha melolontha,Amphimallon solstitialis and Costelytra zealandica.

From the order of the Hymenoptera, for example, Diprion spp., Hoplocampaspp., Lasius spp., Monomoriumpharaonis and Vespa spp.

From the order of the Diptera, for example, Aedes spp., Anopheles spp.,Culex spp., Drosophila melanogaster, Musca spp., Fannia spp., Calliphoraerythrocephala, Lucilia spp., Chrysomyia spp., Cuterebra spp.,Gastrophilus spp., Hyppobosca spp., Stomoxys spp., Oestrus spp.,Hypoderma spp., Tabanus spp., Tannia spp., Bibio hortulanus, Oscinellafrit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae,Tipula paludosa, Hylemyia spp. and Liriomyza spp.

From the order of the Siphonaptera, for example, Xenopsylla cheopis andCeratophyllus spp.

From the order of the Arachnida, for example, Scorpio maurus,Latrodectus mactans. Acarus siro, Argas spp., Omithodoros spp.,Dernanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora,Boophilus spp., Rhipicephalus spp., Amblyomma spp., Hyalomma spp.,Ixodes spp., Psoroptes spp., Chorioptes spp., Sarcoptes spp., Tarsonemusspp., Bryobia praetiosa, Panonychus spp., Tetranychus spp.,Hemitarsonemus spp., Brevipalpus spp.

The phytoparasitic nematodes include, for example, Pratylenchus spp.,Radopholus similis, Ditylenchus dipsaci, Tylenchulus semipenetrans,Heterodera spp., Globodera spp., Meloidogyne spp., Aphelenchoides spp.,Longidorus spp., Xiphinema spp., Trichodorus spp., Bursaphelenchus spp.

The active compounds according to the invention have high insecticidaland acaridical activity after foliar and soil application.

They can be employed particularly successfully for controllingplant-damaging insects, such as, for example, against the larvae of themustard beetle (Phaedon cochleariae), against the larvae of the greenrice leafhopper (Nephotettix cincticeps) and against the larvae of thegreen peach aphid (Myzus persicae).

The active compounds can be converted to the customary formulations,such as solutions, emulsions, wettable powders, suspensions, powders,dusts, pastes, soluble powders, granules, suspension-emulsionconcentrates, natural and synthetic materials impregnated with activecompound and microencapsulationsin polymeric substances.

These formulations are produced in a known manner, for example by mixingthe active compounds with extenders, that is, liquid solvents, and/orsolid carriers, optionally with the use of surfactants, that isemulsifiers and/or dispersants, and/or foam-formers.

If the extender used is water, it is also possible to employ for exampleorganic solvents as auxiliary solvents. Essentially, suitable liquidsolvents are: aromatics such as xylene, toluene or alkylnaphthalenes,chlorinated aromatics or chlorinated aliphatic hydrocarbons such aschlorobenzenes, chloroethylenes or methylene chloride, aliphatichydrocarbons such as cyclohexane or paraffins, for example petroleumfractions, mineral and vegetable oils, alcohols such as butanol orglycol and also their ethers and esters, ketones such as acetone, methylethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polarsolvents such as dimethylformamide and dimethyl sulphoxide, and alsowater.

As solid carriers there are suitable:

-   for example ammonium salts and ground natural minerals such as    kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or    diatomaceous earth, and ground synthetic minerals, such as highly    disperse silica, alumina and silicates; as solid carriers for    granules there are suitable: for example crushed and fractionated    natural rocks such as calcite, marble, pumice, sepiolite and    dolomite, and also synthetic granules of inorganic and organic    meals, and granules of organic material such as sawdust, coconut    shells, maize cobs and tobacco stalks; as emulsifiers and/or    foam-formers there are suitable: for example nonionic and anionic    emulsifiers, such as polyoxyethylene fatty acid esters,    polyoxyethylene fatty alcohol ethers, for example alkylaryl    polyglycol ethers, alkylsulphonates, alkyl sulphates,    arylsulphonates and also protein hydrolysates; as dispersants there    are suitable: for example lignin-sulphite waste liquors and    methylcellulose.

Tackifiers such as carboxymethylcellulose and natural and syntheticpolymers in the form of powders, granules or latices, such as gumarabic, polyvinyl alcohol and polyvinyl acetate, as well as naturalphospholipids such as cephalins and lecithins, and syntheticphospholipids, can be used in the formulations. Other additives can bemineral and vegetable oils.

It is possible to use colorants such as inorganic pigments, for exampleiron oxide, titanium oxide and Prussian Blue, and organic dyestuffs,such as alizarin dyestuffs, azo dyestuffs and metal phthalocyaninedyestuffs, and trace nutrients such as salts of iron, manganese, boron,copper, cobalt, molybdenum and zinc.

The formulations generally comprise between 0.1 and 95% by weight ofactive compound, preferably between 0.5 and 90%.

The active compound according to the invention can be present in itscommercially available formulations and in the use forms, prepared fromthese formulations, as a mixture with other active compounds, such asinsecticides, attractants, sterilizing agents, bactericides, acaricides,nematicides, fungicides, growth-regulating substances or herbicides. Theinsecticides include, for example, phosphoric acid esters, carbamates,carboxylates, chlorinated hydrocarbons, phenylureas and substancesproduced by microorganisms, inter alia.

Particularly favourable examples of co-components in mixtures are thefollowing compounds:

Fungicides:

-   aldimorph, ampropylfos, ampropylfos potassium, andoprim, anilazine,    azaconazole, azoxystrobin, benalaxyl, benodanil, benomyl,    benzamacril, benzamacryl-isobutyl, bialaphos, binapacryl, biphenyl,    bitertanol, blasticidin-S, bromuconazole, bupirimate, buthiobate,    calcium polysulphide, capsimycin, captafol, captan, carbendazim,    carboxin, carvon, quinomethionate, chlobenthiazone, chlorfenazole,    chloroneb, chloropicrin, chlorothalonil, chlozolinate, clozylacon,    cufraneb, cymoxanil, cyproconazole, cyprodinil, cyprofuram,-   debacarb, dichlorophen, diclobutrazole, diclofluanid, diclomezine,    dicloran, diethofencarb, difenoconazole, dimethirimol, dimethomorph,    diniconazole, diniconazole-M, dinocap, diphenylamine, dipyrithione,    ditalimfos, dithianon, dodemorph, dodine, drazoxolon,-   edifenphos, epoxiconazole, etaconazole, ethirimol, etridiazole,-   famoxadon, fenapanil, fenarimol, fenbuconazole, fenfuram,    fenitropan, fenpiclonil, fenpropidin, fenpropimorph, fentin acetate,    fentin hydroxide, ferbam, ferimzone, fluazinam, flumetover,    fluoromide, fluquinconazole, flurprimidol, flusilazole,    flusulfamide, flutolanil, flutriafol, folpet, fosetyl-aluminium,    fosetyl-sodium, fthalide, filberidazole, furalaxyl, furametpyr,    furcarbonil, furconazole, furconazole-cis, furmecyclox,-   guazatine,-   hexachlorobenzene, hexaconazole, hymexazole,-   imazalil, imibenconazole, iminoctadine, iminoctadine albesilate,    iminoctadine triacetate, iodocarb, ipconazole, iprobenfos (IBP),    iprodione, irumamycin, isoprothiolane, isovaledione,-   kasugamycin, kresoxim-methyl, copper preparations, such as: copper    hydroxide, copper naphthenate, copper oxychloride, copper sulphate,    copper oxide, oxine-copper and Bordeaux mixture,-   mancopper, mancozeb, maneb, meferimzone, mepanipyrim, mepronil,    metalaxyl, metconazole, methasulfocarb, methfiuroxam, metiram,    metomeclam, metsulfovax, mildiomycin, myclobutanil, myclozolin,-   nickel dimethyldithiocarbamate, nitrothal-isopropyl, nuarimol,-   ofurace, oxadixyl, oxamocarb, oxolinic acid, oxycarboxim,    oxyfenthiin,-   paclobutrazole, pefurazoate, penconazole, pencycuron, phosdiphen,    pimaricin, piperalin, polyoxin, polyoxorim, probenazole, prochloraz,    procymidone, propamocarb, propanosine-sodium, propiconazole,    propineb, pyrazophos, pyrifenox, pyrimethanil, pyroquilon,    pyroxyfur,-   quinconazole, quintozene (PCNB),-   sulphur and sulphur preparations,-   tebuconazole, tecloftalam, tecnazene, tetcyclasis, tetraconazole,    thiabendazole, thicyofen, thifluzamide, thiophanate-methyl, thiram,    tioxymid, tolclofos-methyl, tolylfluanid, triadimefon, triadimenol,    triazbutil, triazoxide, trichlamide, tricyclazole, tridemorph,    triflumizole, triforine, triticonazole,-   uniconazole,-   validamycin A, vinclozolin, viniconazole,-   zarilamide, zineb, ziramn and also-   Dagger G,-   OK-8705,-   OK-8801,-   α-(1,1-dimethylethyl)-β-(2-phenoxyethyl)-1H-1,2,4-triazole-1-ethanol,-   α-(2,4-dichlorophenyl)-β-fluoro-β-propyl-1H-1,2,4-triazole-1-ethanol,-   α-(2,4-dichlorophenyl)-β-methoxy-αmethyl-1H-1,2,4-triazole-1-ethanol,-   α-(5-methyl-1,3-dioxan-5-yl)-β-[[4-(trifluoromethyl)-phenyl]-methylene]-1H-1,2,4-triazole-1-ethanol,-   (5RS,6RS)-6-hydroxy-2,2,7,7-tetramethyl-5-(1H-1,2,4-triazol-1-yl)-3-octanone,-   (E)-α-(methoxyimino)-N-methyl-2-phenoxy-phenylacetamide,-   1-isopropyl{2-methyl-1-[[[1-(4-methylphenyl)-ethyl]-amino]carbonyl]-propyl}-carbamate,-   1-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-yl)-ethanone-O-(phenylmethyl)-oxime,-   1-(2-methyl-1-naphthalenyl)-1H-pyrrol-2,5-dione,-   1-(3,5-dichlorophenyl)-3-(2-propenyl)-2,5-pyrrolidindione,-   1-[(diiodomethyl)-sulphonyl]-4-methyl-benzene,-   1-[[2-(2,4-dichlorophenyl)-1,3-dioxolan-2-yl]-methyl]-1H-imidazole,-   1-[[2-(4-chlorophenyl)-3-phenyloxiranyl]-methyl]-1H-1,2,4-triazole,-   1-[1-[2-[(2,4-dichlorophenyl)-methoxy]-phenyl]-ethenyl]-1H-imidazole,-   1-methyl-5-nonyl-2-(phenylmethyl)-3-pyrrolidinole,-   2′,6′-dibromo-2-methyl-4′-trifluoromethoxy-4′-trifluoro-methyl-1,3-thiazole-5-carboxanilide,-   2,2-dichloro-N-[1-(4-chlorophenyl)-ethyl]-1-ethyl-3-methyl-cyclopropanecarboxamide,-   2,6-dichloro-5-(methylthio)-4-pyrimidinyl-thiocyanate,-   2,6-dichloro-N-(4-trifluoromethylbenzyl)-benzamide,-   2,6-dichloro-N-[[4-(trifluoromethyl)-phenyl]-methyl]-benzamide,-   2-(2,3,3-triiodo-2-propenyl)-2H-tetrazole,-   2-[(1-methylethyl)-sulphonyl]-5-(trichloromethyl)-1,3,4-thiadiazole,-   2-[[6-deoxy-4-O-(4-O-methyl-β-D-glycopyranosyl)-α-D-glucopyranosyl]-amino]-4-methoxy-1H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile,-   2-aminobutane,-   2-bromo-2-(bromomethyl)-pentanedinitrile,-   2-chloro-N-(2,3-dihydro-1,1,3-trimethyl-1H-inden-4-yl)-3-pyridinecarboxamide,-   2-chloro-N-(2,6-dimethylphenyl)-N-(isothiocyanatomethyl)-acetamide,-   2-phenylphenol (OPP),-   3,4-dichloro-1-[4-(difluoromethoxy)-phenyl]-1H-pyrrol-2,5-dione,-   3,5-dichloro-N-[cyano[(1-methyl-2-propynyl)-oxy]-methyl]-benzamide,-   3-(1,1-dimethylpropyl-1-oxo-1H-indene-2-carbonitrile,-   3-[2-(4-chlorophenyl)-5-ethoxy-3-isoxazolidinyl]-pyridine,-   4-chloro-2-cyano-N,N-dimethyl-5-(4-methylphenyl)-1H-imidazole-1-sulphonamide,-   4-methyl-tetrazolo[1,5-a]quinazolin-5-(4H)-one,-   8-(1,1-dimethylethyl)-N-ethyl-N-propyl-1,4-dioxaspiro[4.5]decane-2-methanamine,-   8-hydroxyquinolinesulphate,-   9H-xanthene-2-[(phenylamino)-carbonyl]-9-carboxylihydrazide,-   bis-(1-methylethyl)-3-methyl-4-[(3-methylbenzoyl)-oxy]-2,5-thiophenedicarboxylate,-   cis-1-(4-chlorophenyl)-2-(1H-1,2,4-triazol-1-yl)-cycloheptanol,-   cis-4-[3-[4-(1,1-dimethylpropyl)-phenyl-2-methylpropyl]-2,6-dimethyl-morpholine    hydrochloride,-   ethyl[(4-chlorophenyl)-azo]-cyanoacetate,-   potassium bicarbonate,-   methanetetrathiol-sodiumsalt,-   methyl    1-(2,3-dihydro-2,2-dimethyl-1H-inden-1-yl)-1H-imidazole-5-carboxylate,-   methyl N-(2,6-dimethylphenyl)-N-(5-isoxazolylcarbonyl)-DL-alaninate,-   methyl N-(chloroacetyl)-N-(2,6-dimethylphenyl)-DL-alaninate,-   N-(2,3-dichloro-4-hydroxyphenyl)-1-methyl-cyclohexanecarboxamide,-   N-(2,6-dimethylphenyl)-2-methoxy-N-(tetrahydro-2-oxo-3-furanyl)-acetamide,-   N-(2,6-dimethylphenyl)-2-methoxy-N-(tetrahydro-2-oxo-3-thienyl)-acetamide,-   N-(2-chloro-4-nitrophenyl)-4-methyl-3-nitro-benzenesulphonamide,-   N-(4-cyclohexylphenyl)-1,4,5,6-tetrahydro-2-pyrimidinamine,-   N-(4-hexylphenyl)-1,4,5,6-tetrahydro-2-pyrimidinamine,-   N-(5-chloro-2-methylphenyl)-2-methoxy-N-(2-oxo-3-oxazolidinyl)-acetamide,-   N-(6-methoxy)-3-pyridinyl)-cyclopropanecarboxamide,-   N-[2,2,2-trichloro-1-[(chloroacetyl)-amino]-ethyl]-benzamide,-   N-[3-chloro-4,5-bis(2-propinyloxy)-phenyl]-N′-methoxy-methanimidamide,-   N-formyl-N-hydroxy-DL-alanine-sodium salt,-   O,O-diethyl    [2-(dipropylamino)-2-oxoethyl]-ethylphosphoramidothioate,-   O-methyl S-phenyl phenylpropylphosphoramidothioate,-   S-methyl 1,2,3-benzothiadiazole-7-carbothioate,-   spiro[2H]-1-benzopyrane-2,1′(3′H)-isobenzofuran)-3′-one,    Bactericides:-   bronopol, dichlorophen, nitrapyrin, nickel dimethyldithiocarbamate,    kasugamycin, octhilinone, furancarboxylic acid, oxytetracyclin,    probenazole, streptomycin, tecloftalam, copper sulphate and other    copper preparations.    Insecticides/Acaricides/Nematicides:-   abamectin, acephate, acetamiprid, acrinathrin, alanycarb, aldicarb,    aldoxycarb, alphacyperrnethrin, alphamethrin, amitraz, avernectin,    AZ 60541, azadirachtin, azamethiphos, azinphos A, azinphos M,    azocyclotin,-   Bacillus popilliae, Bacillus sphaericus, Bacillus subtilis, Bacillus    thuringiensis, baculoviruses, Beauveria bassiana, Beauveria tenella,    bendiocarb, benfuracarb, bensultap, benzoximate, betacyfluthrin,    bifenazate, bifenthrin, bioethanomethrin, biopermethrin, BPMC,    bromophos A, bufencarb, buprofezin, butathiofos, butocarboxim,    butylpyridaben,-   cadusafos, carbaryl, carbofuran, carbophenothion, carbosulfan,    cartap, chloethocarb, chlorethoxyfos, chlorfenapyr, chlorfenvinphos,    chlorfluazuron, chlormephos, chlorpyrifos, chlorpyrifos M,    chlovaporthrin, cis-resmethrin, cispermethrin, clocythrin,    cloethocarb, clofentezine, cyanophos, cycloprene, cycloprothrin,    cyfluthrin, cyhalothrin, cyhexatin, cypermethrin, cyromazine,-   deltamethrin, demeton M, demeton S, demeton-S-methyl, diafenthiuron,    diazinon, dichlorvos, diflubenzuron, dimethoate, dimethylvinphos,    diofenolan, disulfoton, docusat-sodium, dofenapyn,-   eflusilanate, emamectin, empenthrin, endosulfan, Entomopfthora spp.,    esfenvalerate, ethiofencarb, ethion, ethoprophos, etofenprox,    etoxazole, etrimfos,-   fenamiphos, fenazaquin, fenbutatin oxide, fenitrothion,    fenothiocarb, fenoxacrim, fenoxycarb, fenpropathrin, fenpyrad,    fenpyrithrin, fenpyroximate, fenvalerate, fipronil, fluazinam,    fluazuron, flubrocythrinate, flucycloxuron, flucythrinate,    flufenoxuron, flutenzine, fluvalinate, fonophos, fosmethilan,    fosthiazate, fubfenprox, furathiocarb,-   granulosis viruses,-   halofenozide, HCH, heptenophos, hexaflumuron, hexythiazox,    hydroprene,-   imidacloprid, isazofos, isofenphos, isoxathion, ivermectin,-   nuclear polyhedrosis viruses,-   lambda-cyhalothrin, lufenuron,-   malathion, mecarbam, metaldehyde, methamidophos, Metharhizium    anisopliae, Metharhizium flavoviride, methidathion, methiocarb,    methomyl, methoxyfenozide, metolcarb, metoxadiazone, mevinphos,    milbemectin, monocrotophos,-   naled, nitenpyram, nithiazine, novaluron,-   omethoate, oxamyl, oxydemethon M,-   Paecilomyces fumosoroseus, parathion A, parathion M, permethrin,    phenthoate, phorate, phosalone, phosmet, phosphamidon, phoxim,    pirimicarb, pirimiphos A, pirimiphos M, profenofos, promecarb,    propoxur, prothiofos, prothoate, pymetrozine, pyraclofos,    pyresmethrin, pyrethrum, pyridaben, pyridathion, pyrimidifen,    pyriproxyfen,-   quinalphos,-   ribavirin,-   salithion, sebufos, silafluofen, spinosad, sulfotep, sulprofos,-   tau-fluvalinate, tebufenozide, tebufenpyrad, tebupirimiphos,    teflubenzuron, tefluthrin, temephos, temivinphos, terbufos,    tetrachlorvinphos, theta-cypermethrin, thiapronil, thiatriphos,    thiocyclam hydrogen oxalate, thiodicarb, thiofanox, thuringiensin,    tralocythrin, tralomethrin, triarathene, triazamate, triazophos,    triazuron, trichlophenidine, trichlorfon, triflumuron, trimethacarb,-   vamidothion, vaniliprole, Verticillium lecanii,-   YI 5302,-   zeta-cypermethrin, zolaprofos,-   (1R-cis)[5-(phenylmethyl)-3-furanyl]-methyl-3-[(dihydro-2-oxo-3(2H)-furanylidene)-methyl]-2,2-dimethylcyclopropanecarboxylate,-   (3-phenoxyphenyl)-methyl-2,2,3,3-tetramethylcyclopropanecarboxylate,-   1-[(2-chloro-5-thiazolyl)methyl]tetrahydro-3,5-dimethyl-N-nitro-1,3,5-triazine-2(1H)-imine,-   2-(2-chloro-6-fluorophenyl)-4-[4-(1,1-dimethylethyl)phenyl]-4,5-dihydro-oxazole,-   2-(acetyloxy)-3-dodecyl-1,4-naphthalenedione,-   2-chloro-N-[[[4-(1-phenylethoxy)-phenyl]-amino]-carbonyl]-benzamide,-   2-chloro-N-[[[4-(2,2-dichloro-1,1-difluoroethoxy)-phenyl]-amino]-carbonyl]-benzamide,-   3-methylphenyl propylcarbamate.-   4-[4-(4-ethoxyphenyl)-4-methylpentyl]-1-fluoro-2-phenoxy-benzene,-   4-chloro-2-(1,1-dimethylethyl)-5-[[2-(2,6-dimethyl-4-phenoxyphenoxy)ethyl]thio]-3(2H)-pyridazinone,-   4-chloro-2-(2-chloro-2-methylpropyl)-5-[(6-iodo-3-pyridinyl)methoxy]-3(2H)-pyridazinone,-   4-chloro-5-[(6-chloro-3-pyridinyl)methoxy]-2-(3,4-dichlorophenyl)-3(2H)-pyridazinone,-   Bacillus thuringiensis strain EG-2348,-   [2-benzoyl-1-(1,1-dimethylethyl)-hydrazinobenzoic acid,-   2,2-dimethyl-3-(2,4-dichlorophenyl)-2-oxo-1-oxaspiro[4.5]dec-3-en-4-yl    butanoate,-   [3-[(6-chloro-3-pyridinyl)methyl]-2-thiazolidinylidene]-cyanamide,-   dihydro-2-(nitromethylene)-2H-1,3-thiazine-3 (4H)-carboxaldehyde,-   ethyl    [2-[[1,6-dihydro-6-oxo-1-(phenylmethyl)-4-pyridazinyl]oxy]ethyl]-carbamate,-   N-(3,4,4-trifluoro-1-oxo-3-butenyl)-glycine,-   N-(4-chlorophenyl)-3-[4-(difluoromethoxy)phenyl]-4,5-dihydro-4-phenyl-1H-pyrazole-1-carboxamide,-   N-[(2-chloro-5-thiazolyl)methyl]-N′-methyl-N″-nitro-guanidine,-   N-methyl-N′-(1-methyl-2-propenyl)-1,2-hydrazinedicarbothioamide,-   N-methyl-N′-2-propenyl-1,2-hydrazinedicarbothioamide,-   O,O-diethyl    [2-(dipropylamino)-2-oxoethyl]-ethylphosphoramidothioate.

It is also possible to admix other known active compounds, such asherbicides, fertilizers and growth regulators.

When used as insecticides, the active compounds according to theinvention can furthermore be present in their commercially availableformulations and in the use forms, prepared from these formulations, asa mixture with synergistic agents. Synergistic agents are compoundswhich increase the action of the active compounds, without it beingnecessary for the synergistic agent added to be active itself.

The active compound content of the use forms prepared from thecommercially available formulations can vary within wide limits. Theactive compound concentration of the use forms can be from 0.0000001 to95% by weight of active compound, preferably between 0.0001 and 1% byweight.

The compounds are employed in a customary manner appropriate for the useforms.

When used against hygiene pests and pests of stored products, the activecompound is distinguished by an excellent residual action on wood andclay as well as a good stability to alkali on limed substrates.

The active compounds according to the invention can be used asdefoliants, desiccants, haulm killers and, especially, as weed killers.By weeds in the broadest sense, there are to be understood all plantswhich grow in locations where they are not wanted. Whether thesubstances according to the invention act as total or selectiveherbicides depends essentially on the amount used.

The active compounds according to the invention can be used, forexample, in connection with the following plants:

Dicotyledonous weeds of the genera: Sinapis, Lepidium, Galium,Stellaria, Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica,Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea,Polygonum, Sesbania, Ambrosia, Cirsium, Carduus, Sonchus, Solanum,Rorippa, Rotala, Lindernia, Lamium, Veronica, Abutilon, Emex, Datura,Viola, Galeopsis, Papaver, Centaurea, Trifolium, Ranunculus andTaraxacum.

Dicotyledonous cultures of the genera: Gossypium, Glycine, Beta, Daucus,Phaseolus, Pisum, Solanum, Linum, Ipomoea, Vicia, Nicotiana,Lycopersicon, Arachis, Brassica, Lactuca, Cucumis and Cucurbita.

Monocotyledonous weeds of the genera: Echinochloa, Setaria, Panicum,Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus,Avena, Cyperus, Sorghum, Agropyron, Cynodon, Monochoria, Fimbristylis,Sagittaria, Eleocharis, Scirpus, Paspalum, Ischaemum, Sphenoclea,Dactyloctenium, Agrostis, Alopecurus Apera, Aegilopus and Phalaris.

Monocotyledonous cultures of the genera: Oryza, Zea, Triticum, Hordeum,Avena, Secale, Sorghum, Panicum, Saccharum, Ananas, Asparagus andAllium.

However, the use of the active compounds according to the invention isin no way restricted to these genera, but also extends in the samemanner to other plants.

The compounds are suitable, depending on the concentration, for thetotal control of weeds, for example on industrial terrain and railwaytracks, and on paths and squares with or without tree plantings.Equally, the compounds can be employed for the control of weeds inperennial crops for example forests, decorative tree plantings,orchards, vineyards, citrus groves, nut orchards, banana plantations,coffee plantations, tea plantations, rubber plantations, oil palmplantations, cocoa plantations, soft fruit plantings and hopfields, inlawns, turf and pasture-land, and for the selective control of weeds inannual crops.

The compounds of the formula (I) according to the invention have strongherbicidal activity and a broad activity spectrum when applied to thesoil and to the above-ground parts of the plants. To a certain extent,they are also suitable for the selective control of monocotyledonous anddicotyledonous weeds in moncotyledonous and dicotyledonous crops, bothpre-emergence and post-emergence.

For the control of weeds, the active compounds according to theinvention, as such or in the form of their formulations, can also beused as mixtures with known herbicides, finished formulations or tankmixes being possible.

Possible components for the mixtures are known herbicides, for example

-   acetochlor, acifluorfen(-sodium), aclonifen, alachlor,    alloxydim(-sodium), ametryne, amidochlor, amidosulfuron, anilofos,    asulam, atrazine, azafanedin, azimsulfuron, benazolin(-ethyl),    benfuresate, bensulfuron(-methyl), bentazon, benzofenap,    benzoylprop(-ethyl), bialaphos, bifenox, bispyribac(-sodium),    bromobutide, bromofenoxim, bromoxynil, butachlor, butroxydim,    butylate, cafenstrole, caloxydim, carbetamide,    carfentrazone(-ethyl), chlomethoxyfen, chloramben, chloridazon,    chlorimuron(-ethyl), chlornitrofen, chlorsulfuron, chlortoluron,    cinidon(-ethyl), cinmethylin, cinosulfuron, clethodim,    clodinafop(-propargyl), clomazone, clomeprop, clopyralid,    clopyrasulfuron(-methyl), cloransulam(-methyl), cumyluron,    cyanazine, cybutryne, cycloate, cyclosulfamuron, cycloxydim,    cyhalofop(-butyl), 2,4-D, 2,4-DB, 2,4-DP, desmedipham, diallate,    dicamba, diclofop(-methyl), diclosulam, diethathyl(-ethyl),    difenzoquat, diflufenican, diflufenzopyr, dimefuron, dimepiperate,    dimethachlor, dimethametryn, dimethenamid, dimexyflam, dinitramine,    diphenamid, diquat, dithiopyr, diuron, dymron, epoprodan, EPTC,    esprocarb, ethalfluralin, ethametsulfuron(-methyl), ethofumesate,    ethoxyfen, etobenzanid, fenoxaprop(-P-ethyl), flamprop(-isopropyl),    flamprop(-isopropyl-L), flamprop(-methyl), flazasulfuron,    fluazifop(-P-butyl), fluazolate, flucarbazone, flufenacet,    flumetsulam, flumiclorac(-pentyl), flumioxazin, flumipropyn,    flumetsulam, fluometuron, fluorochloridone, fluoroglycofen(-ethyl),    flupoxam, flupropacil, flurpyrsulfuron(-methyl, -sodium),    flurenol(-butyl), fluridone, fluroxypyr(-meptyl), flurprimidol,    flurtamone, fluciathet(-methyl), fluthiamide, fomesafen,    glufosinate(-ammonium), glyphosate(-isopropylammonium), halosafen,    haloxyfop (-ethoxyethyl), haloxyfop(-P-methyl), hexazinone,    imazamethabenz(-methyl), imazamethapyr, imazamox, imazapic,    imazapyr, imazaquin, imazethapyr, imazosulfuron, iodosulfuron,    ioxynil, isopropalin, isoproturon, isouron, isoxaben,    isoxachlortole, isoxaflutole, isoxapyrifop, lactofen, lenacil,    linuron, MCPA, MCPP, mefenacet, mesotrione, metamitron, metazachlor,    methabenzthiazuron, metobenzuron, metobromuron, (alpha-)metolachlor,    metosulam, metoxuron, metribuzin, metsulfuron(-methyl), molinate,    monolinuron, naproanilide, napropamide, neburon, nicosulfuron,    norflurazon, orbencarb, oryzalin, oxadiargyl, oxadiazon,    oxasulfuron, oxaziclomefone, oxyfluorfen, paraquat, perlagon acid,    pendimethalin, pentoxazone, phenmedipham, piperophos, pretilachlor,    primisulfuron(-methyl), prometryn, propachlor, propanil,    propaquizafop, propisochlor, propyzamide, prosulfocarb, prosulfuron,    pyraflufen(-ethyl), pyrazolate, pyrazosulfuron(-ethyl), pyrazoxyfen,    pyribenzoxim, pyributicarb, pyridate, pyriminobac(-methyl),    pyrithiobac(-sodium), quinchlorac, quinmerac, quinoclamine,    quizalofop(-ethyl), quizalofop(-p-tefuryl), rimsulfuron, sethoxydim,    simazine, simetryn, sulcotrione, sulfentrazone,    sulfometuron(-methyl), sulfosate, sulfosulfuron, tebutam,    tebuthiuron, tepraloxydim, terbuthylazine, terbutryn, thenylchlor,    thiafluamide, thiazopyr, thidiazimin, thifensulfuron(-methyl),    thiobencarb, tiocarbazil, tralkoxydim, triallate, triasulfuron,    tribenuron(-methyl), triclopyr, tridiphane, trifluralin and    triflusulfuron.

Mixtures with other known active compounds, such as fungicides,insecticides, acaricides, nematicides, bird repellents, plant nutrientsand agents which improve soil structure, are also possible.

The active compounds can be used as such, in the form of theirformulations or in the use forms prepared therefrom by further dilution,such as ready-to-use solutions, suspensions, emulsions, powders, pastesand granules. They are used in the customary manner, for example bywatering, spraying, atomizing or scattering.

The active compounds according to the invention can be applied eitherbefore or after emergence of the plants. They can also be incorporatedinto the soil before sowing.

The amount of active compound used can vary within a substantial range.It depends essentially on the nature of the desired effect. In general,the amounts used are between 1 g and 10 kg of active compound perhectare of soil surface, preferably between 5 g and 5 kg per ha

The active compounds according to the invention act not only againstplant, hygiene and stored product pests, but also in the veterinarymedicine sector against animal parasites (ectoparasites), such as hardticks, soft ticks, mange mites, leaf mites, flies (biting and licking),parasitic fly larvae, lice, hair lice, feather lice and fleas. Theseparasites include:

From the order of the Anoplurida, for example, Haematopinus spp.,Linognathus spp., Pediculus spp., Phtirus spp. and Solenopotes spp.

From the order of the Mallophagida and the suborders Amblycerina andIschnocerina, for example, Trimenopon spp., Menopon spp., Trinoton spp.,Bovicola spp., Werneckiella spp., Lepikentron spp., Damalina spp.,Trichodectes spp. and Felicola spp.

From the order of the Diptera and the suborders Nematocerina andBrachycerina, for example, Aedes spp., Anopheles spp., Culex spp.,Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzomyia spp.,Culicoides spp., Chrysops spp., Hybomitra spp., Atylotus spp., Tabanusspp., Haematopota spp., Philipomyia spp., Braula spp., Musca spp.,Hydrotaea spp., Stomoxys spp., Haematobia spp., Morellia spp., Fanniaspp., Glossina spp., Calliphora spp., Lucilia spp., Chrysomyia spp.,Wohlfahrtia spp., Sarcophaga spp., Oestrus spp., Hypoderma spp.,Gasterophilus spp., Hippobosca spp., Lipoptena spp. and Melophagus spp.

From the order of the Siphonapterida, for example Pulex spp.,Ctenocephalides spp., Xenopsylla spp. and Ceratophyllus spp.

From the order of the Heteropterida, for example, Cimex spp., Triatomaspp., Rhodnius spp. and Panstrongylus spp.

From the order of the Blattarida, for example Blatta orientalis,Periplaneta americana, Blattela germanica and Supella spp.

From the subclass of the Acaria (Acarida) and the orders of the Meta-and Mesostigmata, for example, Argas spp., Ornithodorus spp., Otobiusspp., Ixodes spp., Amblyornma spp., Boophilus spp., Dermacentor spp.,Haemophysalis spp., Hyalomma spp., Rhipicephalus spp., Dermanyssus spp.,Raillietia spp., Pneumonyssus spp., Stemostoma spp. and Varroa spp.

From the order of the Actinedida (Prostigmata) und Acaridida(Astigmata), for example, Acarapis spp., Cheyletiella spp.,Omithocheyletia spp., Myobia spp., Psorergates spp., Demodex spp.,Trombicula spp., Listrophorus spp., Acarus spp., Tyrophagus spp.,Caloglyphus spp., Hypodectes spp., Pterolichus spp., Psoroptes spp.,Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp.,Knemidocoptes spp., Cytodites spp. and Laminosioptes spp.

The active compounds of the formula (I) according to the invention arealso suitable for controlling arthropods which infest agriculturalproductive livestock, such as, for example, cattle, sheep, goats,horses, pigs, donkeys, camels, buffalo, rabbits, chickens, turkeys,ducks, geese and bees, other pets, such as, for example, dogs, cats,caged birds and aquarium fish, and also so-called test animals, such as,for example, hamsters, guinea pigs, rats and mice. By controlling thesearthropods, cases of death and reduction in productivity (for meat,milk, wool, hides, eggs, honey etc.) should be diminished, so that moreeconomic and easier animal husbandry is possible by use of the activecompounds according to the invention.

The active compounds according to the invention are used in theveterinary sector in a known manner by enteral administration in theform of, for example, tablets, capsules, potions, drenches, granules,pastes, boluses, the feed-through process and suppositories, byparenteral administration, such as, for example, by injection(intramuscular, subcutaneous, intravenous, intraperitoneal and thelike), implants by nasal administration, by dermal use in the form, forexample, of dipping or bathing, spraying, pouring on and spotting on,washing and powdering, and also with the aid of molded articlescontaining the active compound, such as collars, ear marks, tail marks,limb bands, halters, marking devices and the like.

When used for cattle, poultry, pets and the like, the active compoundsof the formula (I) can be used as formulations (for example powders,emulsions, free-flowing compositions), which comprise the activecompounds in an amount of 1 to 80% by weight, directly or after 100 to10 000-fold dilution, or they can be used as a chemical bath.

It has furthermore been found that the compounds of the formula (1)according to the invention also have a strong insecticidal actionagainst insects which destroy industrial materials.

The following insects may be mentioned as examples and as preferred—butwithout a limitation:

Beetles, such as

-   Hylotrupes bajulus, Chlorophorus pilosis, Anobium punctatum,    Xestobium rufovillosum, Ptilinus pecticornis, Dendrobium pertinex,    Emobius mollis, Priobium carpini, Lyctus brunneus, Lyctus africanus,    Lyctus planicollis, Lyctus linearis, Lyctus pubescens, Trogoxylon    aequale, Minthes rugicollis, Xyleborus spec. Tryptodendron spec.    Apate monachus, Bostrychus capucins, Heterobostrychus brunneus,    Sinoxylon spec. Dinoderus minutus.

Hymenopterons, such as

-   Sirex juvencus, Urocerus gigas, Urocerus gigas taignus, Urocerus    augur

Termites, such as

-   Kalotermes flavicollis, Cryptotermes brevis, Heteroternes indicola,    Reticulitermes flavipes, Reticulitermes santonensis, Reticulitermes    lucifugus, Mastotermes darwiniensis, Zootermopsis nevadensis,    Coptoternes formosanus.

Bristletails, such as

-   Lepisma saccarina.

Industrial materials in the present connection are to be understood asmeaning non-living materials, such as, preferably, plastics, adhesives,sizes, papers and cards, leather, wood and processed wood products andcoating compositions.

Wood and processed wood products are materials to be protected,especially preferably, from insect infestation.

Wood and wood processed wood products which can be protected by theagents according to the invention or mixtures comprising these are to beunderstood as meaning, for example: building timber, wooden beams,railway sleepers, bridge components, boat jetties, wooden vehicles,boxes, pallets, containers, telegraph poles, wood panelling, woodenwindows and doors, plywood, chipboard, joinery or wooden products whichare used quite generally in house-building or in building joinery.

The active compounds can be used as such, in the form of concentrates orin generally customary formulations, such as powders, granules,solutions, suspensions, emulsions or pastes.

The formulations mentioned can be prepared in a manner known per se, forexample by mixing the active compounds with at least one solvent ordiluent, emulsifier, dispersing agent and/or binder or fixing agent, awater repellent, if appropriate siccatives and UV stabilizers and ifappropriate dyestuffs and pigments, and also other processingauxiliaries.

The insecticidal compositions or concentrates used for the preservationof wood and wood-derived timber products comprise the active compoundaccording to the invention in a concentration of 0.0001 to 95% byweight, in particular 0.001 to 60% by weight.

The amount of the compositions or concentrates employed depends on thenature and occurrence of the insects and on the medium. The optimumamount employed can be determined for the use in each case by a seriesof tests. In general, however, it is sufficient to employ 0.0001 to 20%by weight, preferably 0.001 to 10% by weight, of the active compound,based on the material to be preserved.

Solvents and/or diluents which are used are an organic chemical solventor solvent mixture and/or an oily or oil-like organic chemical solventor solvent mixture of low volatility and/or a polar organic chemicalsolvent or solvent mixture and/or water, and if appropriate anemulsifier and/or wetting agent.

Organic chemical solvents which are preferably used are oily or oil-likesolvents having an evaporation number above 35 and a flashpoint above30° C., preferably above 45° C. Substances which are used as such oilyor oil-like water-insoluble solvents of low volatility are appropriatemineral oils or aromatic fractions thereof, or solvent mixturescontaining mineral oils, preferably white spirit, petroleum and/oralkylbenzene.

Mineral oils having a boiling range from 170 to 220° C., white spirithaving a boiling range from 170 to 220° C., spindle oil having a boilingrange from 250 to 350° C., petroleum and aromatics having a boilingrange from 160 to 280° C., terpentine oil and the like, areadvantageously employed.

In a preferred embodiment, liquid aliphatic hydrocarbons having aboiling range from 180 to 210° C. or high-boiling mixtures of aromaticand aliphatic hydrocarbons having a boiling range from 180 to 220° C.and/or spindle oil and/or monochloronaphthalene, preferablyα-monochloronaphthalene, are used.

The organic oily or oil-like solvents of low volatility which have anevaporation number above 35 and a flashpoint above 30° C., preferablyabove 45° C., can be replaced in part by organic chemical solvents ofhigh or medium volatility, providing that the solvent mixture likewisehas an evaporation number above 35 and a flashpoint above 30° C.,preferably above 45° C., and that the insecticide/fungicide mixture issoluble or emulsifiable in this solvent mixture.

According to a preferred embodiment, some of the organic chemicalsolvent or solvent mixture is replaced by an aliphatic polar organicchemical solvent or solvent mixture. Aliphatic organic chemical solventscontaining hydroxyl and/or ester and/or ether groups, such as, forexample, glycol ethers, esters or the like, are preferably used.

Organic chemical binders which are used in the context of the presentinvention are the synthetic resins and/or binding drying oils which areknown per se, are water-dilutable and/or are soluble or dispersible oremulsifiable in the organic chemical solvents employed, in particularbinders consisting of or comprising an acrylate resin, a vinyl resin,for example polyvinyl acetate, polyester resin, polycondensation orpolyaddition resin, polyurethane resin, alkyd resin or modified alkydresin, phenolic resin, hydrocarbon resin, such as indene-cumarone resin,silicone resin, drying vegetable oils and/or drying oils and/orphysically drying binders based on a natural and/or synthetic resin.

The synthetic resin used as the binder can be employed in the form of anemulsion, dispersion or solution. Bitumen or bituminous substances canalso be used as binders in an amount of up to 10% by weight. Dyestuffs,pigments, water-repelling agents, odour correctants and inhibitors oranticorrosive agents and the like which are known per se canadditionally be employed.

It is preferred according to the invention for the composition orconcentrate to comprise, as the organic chemical binder, at least onealkyd resin or modified alkyd resin and/or one drying vegetable oil.Alkyd resins having an oil content of more than 45% by weight,preferably 50 to 68% by weight, are preferably used according to theinvention.

All or some of the binder mentioned can be replaced by a fixing agent(mixture) or a plasticizer (mixture). These additives are intended toprevent evaporation of the active compounds and crystallization orprecipitation. They preferably replace 0.01 to 30% of the binder (basedon 100% of the binder employed).

The plasticizers originate from the chemical classes of phthalic acidesters, such as dibutyl, dioctyl or benzyl butyl phthalate, phosphoricacid esters, such, as tributyl phosphate, adipic acid esters, such asdi-(2-ethylhexyl) adipate, stearates, such as butyl stearate or amylstearate, oleates, such as butyl oleate, glycerol ethers or highermolecular weight glycol ethers, glycerol esters and p-toluenesulphonicacid esters.

Fixing agents are based chemically on polyvinyl alkyl ethers, such as,for example, polyvinyl methyl ether or ketones, such as benzophenone orethylenebenzophenone.

Possible solvents or diluents are, in particular, also water, ifappropriate as a mixture with one or more of the abovementioned organicchemical solvents or diluents, emulsifiers and dispersing agents.

Particularly effective preservation of wood is achieved by impregnationprocesses on a large industrial scale, for example vacuum, double vacuumor pressure processes.

The ready-to-use compositions can also comprise other insecticides, ifappropriate, and also one or more fungicides, if appropriate.

Possible additional mixing partners are, preferably, the insecticidesand fungicides mentioned in WO 94/29 268. The compounds mentioned inthis document are an explicit constituent of the present application.

Especially preferred mixing partners which may be mentioned areinsecticides, such as chlorpyriphos, phoxim, silafluofin, alphamethrin,cyfluthrin, cypermethrin, deltamethrin, permethrin, imidacloprid, NI-25,flufenoxuron, hexaflumuron and triflumuron, and also fungicides, such asepoxyconazole, hexaconazole, azaconazole, propiconazole, tebuconazole,cyproconazole, metconazole, imazalil, dichlorfluanid, tolylfluanid,3-iodo-2-propinyl-butyl carbamate, N-octyl-isothiazolin-3-one and4,5-dichloro-N-octylisothiazolin-3-one.

The preparation and the use of the active compounds according to theinvention is illustrated by the examples below.

EXAMPLE

Myzus Test

-   Solvent: 1 part by weight of dimethylformamide-   Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

Cabbage leaves (Brassica oleracea) which are heavily infested by peachaphids (Myzus persicae) are treated by being dipped into the preparationof active compound of the desired concentration.

After the desired period of time, the kill in % is determined. 100%means that all aphids have been killed; 0% means that none of the aphidshave been killed.

In this test, for example, the following compound of the PreparationExamples shows good activity:

TABLE Plant-damaging insects Myzus test Concentration of active Kill in% after Active compound compound in % 6 days Ex. I-1-a-4 0.1 95

EXAMPLE

Nephotettix Test

-   Solvent: 7 parts by weight of dimethylformamide-   Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

Rice seedlings (Oryza sativa) are treated by being dipped into thepreparation of active compound of the desired concentration and arepopulated with larvae of the green rice leaf-hopper (Nephotettixcincticeps) while the leaves are still moist.

After the desired period of time, the kill in % is determined. 100%means that all leaf-hoppers have been killed; 0% means that none of theleaf-hoppers have been killed.

In this test, for example, the following compounds of the PreparationExamples show good activity:

TABLE Plant-damaging insects Nephotettix test Active compound Kill in %after Active compound in % 6 days Ex. I-1-a-3 0.1 100

Ex. I-1-a-4 0.1 100

EXAMPLE

Phaedon Larvae Test

-   Solvent: 7 parts by weights of dimethylformamide-   Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

Cabbage leaves (Brassica oleracea) are treated by being dipped into thepreparation of active compound of the desired concentration and arepopulated with larvae of the mustard beetle (Phaedon cochleariae) whilethe leaves are still moist.

After the desired period of time, the kill in % is determined. 100%means that all aphids have been killed; 0% means that none of the aphidshave been killed.

In this test, for example, the following compounds of the PreparationExamples shows good activity:

TABLE Plant-damaging insects Phaedon larvae test Concentration of activeKill in % after Active compound compound in % 7 days Ex. I-1-a-3 0.1 100

Ex. I-1-a-4 0.1 100

EXAMPLE

Post-Emergence Test

-   Solvent: 5 parts by weight of acetone-   Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, one part by weightof active compound is mixed with the stated amount of solvent, thestated amount of emulsifier is added and the concentrate is diluted withwater to the desired concentration.

Test plants which have a height of 5–15 cm are sprayed with thepreparation of active compound in such a way as to apply the particularamounts of active compound desired per unit area. After 3 weeks, thedegree of damage to the plants is rated in % damage in comparison to thedevelopment of the untreated control.

The figures denote:

-   -   0%=no effect (like untreated control)    -   100%=total destruction

Post-emergence/greenhouse g of ai./ha Sugar beet Avena fatua SetariaSinapis Ex. 250 20 70 100 70 I-1-a-2 g of ai./ha Avena fatua SetariaAbutilon Amaranthus Ex. 250 90 100 80 80 I-1-a-4

EXAMPLE I-1-a-1

Under argon, 1.1 g of3-[(4-bromo-2-ethyl-6-methyl)-phenyl]-5-isopropyl-5-methyl-pyrrolidin-2,4-dioneaccording to Example I-1-a-4 from WO 97/02243 in 20 ml of1,2-dimethoxyethane are admixed with 0.6 g of 4-chlorophenylboronic acidand 180 mg of tetrakis(triphenylphosphine)palladium. The mixture isstirred at 20° C. for 15 min, 15 ml of 20% strength aqueous sodiumcarbonate solution are then added, and the mixture is stirred at 80° C.for one day. The mixture is then filtered, the filtrate is admixed withwater and the aqueous phase is acidified. Filtration with suction gives0.75 g of product (65% of theory).

m.p.: 245° C.

By the method of Example (I-1-a-1) and (I-1-a-43), and/or in accordancewith the general procedures for preparing compounds of the formula(I-1-a), the following compounds of the formula (I-1-a) are obtained:

EXAMPLE

Pre-Emergence Test

-   Solvent: 5 parts by weight of acetone-   Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, one part by weightof active compound is mixed with the stated amount of solvent, thestated amount of emulsifier is added and the concentrate is diluted withwater to the desired concentration.

Seeds of the test plants are sown in normal soil and, after 24 hours,watered with the preparation of the active compound. Advantageously, theamount of water per unit area is kept constant. The active compoundconcentration in the preparation is not important, only the activecompound application rate per unit area matters. After three weeks, thedegree of damage to the plants is rated in % damage in comparison to thedevelopment of the untreated control.

The figures denote:

-   -   0%=no effect (like untreated control)    -   100%=total destruction

Pre-emergence/greenhouse g of ai./ha Alopecurus Setaria AmaranthusGalium Ex. 250 100 100 100 90 I-1-a-3 Ex. No. X Z V¹ V² D A B m.p.° C.isomer I-1-a-2 CH₃ CH₃ 4-Cl H H —(CH₂)₂—CHOCH₃—(CH₂)₂— >240 β I-1-a-3CH₃ Cl 4-Cl H H —(CH₂)₂—CHOCH₃—(CH₂)₂— 211 β I-1-a-4 CH₃ Cl 4-Cl H H—(CH₂)₂—CHOC₂H₅—(CH₂)₂— >230 β I-1-a-5 CH₃ CH₃ 4-Cl H H—CH₂—O—(CH₂)₃— >240 — I-1-a-6 C₂H₅ CH₃ 4-Cl H H CH₃ CH₃ >240 — I-1-a-7C₂H₅ C₂H₅ 4-Cl H H —(CH₂)₂—CHCH₃—(CH₂)₂— 188 β I-1-a-8 CH₃ Cl 4-Cl H H—(CH₂)₂—O—(CH₂)₂— 165–167 — I-1-a-9 C₂H₅ Cl 4-Cl H H—(CH₂)₂—CHOCH₃—(CH₂)₂— >240 β I-1-a-10 C₂H₅ Cl 4-Cl H H—(CH₂)₂—CHCH₃—(CH₂)₂— >240 β I-1-a-11 CH₃ Cl 4-Cl H H i-C₃H₇ CH₃ >240 —I-1-a-12 CH₃ CH₃ 4-Cl H H CH₃ CH₃ >240 — I-1-a-13 C₂H₅ C₂H₅ 4-Cl H Hi-C₃H₇ CH₃ 218 — I-1-a-14 CH₃ CH₃ 4-Cl H H —(CH₂)₅— >240 — I-1-a-15 CH₃CH₃ 3-Cl H H —(CH₂)₂—CHOCH₃—(CH₂)₂— 135 β I-1-a-16 CH₃ CH₃ 2-Cl H H—(CH₂)₂CHOCH₃(CH₂)₂— >245 β I-1-a-17 CH₃ CH₃ 4-Cl H H—(CH₂)₂—O—(CH₂)₂— >235 — I-1-a-18 CH₃ CH₃ 4-Cl H H—(CH₂)₂CHOC₂H₅(CH₂)₂— >245 β I-1-a-19 CH₃ CH₃ 4-Cl H H—(CH₂)₂—CHCH₃—(CH₂)₂— >245 β I-1-a-20 CH₃ CH₃ 4-Cl H H—CH₂—CHCH₃—(CH₂)₃— >245 β I-1-a-21 CH₃ CH₃ 4-Cl H —(CH₂)₄— H >240 —I-1-a-22 CH₃ CH₃ 4-Cl H i-C₃H₇ H H >249 — I-1-a-23 CH₃ CH₃ 2-CH₃ 5-CH₃ H—CH₂—O—(CH₂)₃— 148 — I-1-a-24 CH₃ CH₃ 2-CH₃ 6-CH₃ H —CH₂—O—(CH₂)₃— >250— I-1-a-25 CH₃ CH₃ 3-CH₃ 5-CH₃ H —CH₂—O—(CH₂)₃— >250 — I-1-a-26 CH₃ Cl4-Cl H H —(CH₂)₅— >250 — I-1-a-27 CH₃ Cl 3-CF₃ 5-CF₃ H —(CH₂)₅— >250 —I-1-a-28 CH₃ Cl 3-CF₃ H H —(CH₂)₅— >250 — I-1-a-29 CH₃ Cl 2-Cl 4-Cl H—(CH₂)₅— >250 — I-1-a-30 CH₃ Cl 3-Cl 5-Cl H —(CH₂)₅— >250 — I-1-a-31C₂H₅ C₂H₅ 4-Cl H H —(CH₂)₂—CHCH₃—(CH₂)₂— >250 — I-1-a-32 C₂H₅ C₂H₅ 3-CF₃5-CF₃ H —(CH₂)₂CHCH₃—(CH₂)₂— 242–244 β I-1-a-33 C₂H₅ C₂H₅ 4-CF₃ H H—(CH₂)₂CHCH₃—(CH₂)₂— >250 β I-1-a-34 CH₃ CH₃ 4-Cl H H i-C₃H₇ CH₃ Wax —I-1-a-35 C₂H₅ C₂H₅ 2-Cl 4-Cl H —(CH₂)₂CHCH₃—(CH₂)₂— >250 β I-1-a-36 C₂H₅C₂H₅ 3-Cl 5-Cl H —(CH₂)₂CHCH₃—(CH₂)₂— >250 β I-1-a-37 CH₃ CH₃ 2-Cl 4-ClH i-C₃H₇ CH₃ 115–117 — I-1-a-38 CH₃ CH₃ 3-Cl 5-Cl H i-C₃H₇ CH₃ 233–234 —I-1-a-39 C₂H₅ Cl 4-Cl H H CH₃ CH₃ >250 — I-1-a-40 C₂H₅ Cl 3-Cl 5-Cl HCH₃ CH₃ 125–127 — I-1-a-41 CH₃ Cl 4-Cl H H CH₃ CH₃ >250 — I-1-a-42 CH₃Cl 3-CF₃ 5-CF₃ H CH₃ CH₃ >250 — I-1-a-43 CH₃ CH₃ 4-Cl H H i-C₃H₇CH₃ >250 — I-1-a-44 CH₃ CH₃ 4-CH₃ H H —(CH₂)₂—CHOCH₃—(CH₂)₂— >235 βI-1-a-45 CH₃ CH₃ 2-CH₃ 5-F H —(CH₂)₂—CHOCH₃—(CH₂)₂— >235 β I-1-a-46 CH₃CH₃ 2-CH₃ 5-CH₃ H —(CH₂)₂—CHOCH₃—(CH₂)₂— 168 β I-1-a-47 CH₃ CH₃ 2- H H—(CH₂)₂—CHOCH₃—(CH₂)₂— β OCH₃ I-1-a-48 CH₃ CH₃ 3-CH₃ 5-CH₃ H—(CH₂)₂—CHOCH₃—(CH₂)₂— 238 β I-1-a-49 CH₃ CH₃ 2-Cl 4-Cl H—(CH₂)₂—CHOCH₃—(CH₂)₂— 188 β I-1-a-50 CH₃ CH₃ 2-Cl 3-Cl H—(CH₂)₂—CHOCH₃—(CH₂)₂— >235 β

EXAMPLE I-1-b-1

First 0.67 ml (4.8 mmol) of triethylamine and then, at refluxtemperature, 0.5 ml (0.005 mol) of isobutyryl chloride in 5 ml ofabsolute ethyl acetate are added to 1.58 g of the compound of ExampleI-1-a-19 in 40 ml of absolute ethyl acetate. Stirring is continued atthis temperature until the reaction has ended (monitored by thin-layerchromatography). The mixture is then concentrated and the residue istaken up in methylene chloride, washed twice with 30 ml of 0.5 N NaOH,dried and concentrated. The residue is recrystallized from methyltert-butyl ether (MTBE)/n-hexane. Yield 1.27 g (68% of theory).m.p.:>247° C.

By the method of Example (I-1-b-1), and/or in accordance with thegeneral procedures for preparing compounds of the formula (I-1-b), thefollowing compounds of the formula (I-1-b) are obtained:

(I-1-b)

Ex. No. X Z V¹ V² D A B R¹ m.p. ° C. isomer I-1-b-2 CH₃ CH₃ 4-Cl H H—(CH₂)₂—CHCH₃—(CH₂)₂— H₅C₂—O—CH₂— >247 β I-1-b-3 CH₃ CH₃ 4-Cl H H—CH₂—CHCH₃—(CH₂)₃— i-C₃H₇— >247 β I-1-b-4 CH₃ CH₃ 4-Cl H H—CH₂—CHCH₃—(CH₂)₃—

>254 β I-1-b-5 CH₃ CH₃ 4-Cl H H —CH₂—CHOCH₃—(CH₂)₂— i-C₃H₇— 236 βI-1-b-6 CH₃ CH₃ 4-Cl H H —CH₂—CHOCH₃—(CH₂)₂—

>247 β I-1-b-7 CH₃ CH₃ 3-Cl H H —CH₂—CHOCH₃—(CH₂)₂— i-C₃H₇— 238 β

EXAMPLE I-1-c-1

At −10° C. to 0° C., 0.15 g of chloroformic acid in 5 ml of methylenechloride is added to 0.35 g of the compound of Example I-1-a-12 and 0.15ml of triethylamine in 30 ml of methylene chloride, and the mixture isstirred at room temperature for 2 hours.

The reaction mixture is filtered through silica gel using methylenechloride/ethyl acetate 5:3 as mobile phase, and is then concentrated anddissolved in a little methylene chloride, and the product isprecipitated out by addition of hexane.

Yield 0.23 g (56% of theory). m.p.: 129° C.

By the method of Example (I-1-c-1), and/or according to the generalprocedures for preparing compounds of the formula (I-1-c), the followingcompounds of the formula (I-1-c) are obtained:

(I-1-c)

Ex.- m.p. No. X Z V¹ V² D A B L M R² ° C. isomer I-1-c-2 CH₃ CH₃ 4-Cl HH —(CH₂)₂—CHCH₃—(CH₂)₂— O O C₂H₅— >240 β I-1-c-3 CH₃ CH₃ 4-Cl H H—CH₂—CHCH₃—(CH₂)₃— O O C₂H₅— >240 β I-1-c-4 CH₃ CH₃ 4-Cl H H—(CH₂)₂—CHOCH₃—(CH₂)₂— O O C₂H₅ 202 β I-1-c-5 CH₃ CH₃ 3-Cl H H—(CH₂)₂—CHOCH₃—(CH₂)₂— O O C₂H₅— 214 β I-1-c-6 CH₃ CH₃ 3-Cl H H—(CH₂)₂—CHOCH₃—(CH₂)₂— O O

248 β I-1-c-7 CH₃ CH₃ 3-Cl H H —(CH₂)₂—CHOCH₃—(CH₂)₂— O O

239 β

EXAMPLE I-2-a-1

1.0 g (2.6 mmol) of3-[(2,6-dimethyl-4-bromo)-phenyl]-5,5-[(3-methoxy)-pentamethylene]-4-hydroxy-Δ³-dihydrofuran-2-oneaccording to Example I-2-a-15 from WO 97/02243 is suspended in 20 ml ofdiethoxyethane, 0.5 g (3.2 mmol) of 4-chlorophenylboronic acid and 180mg (0.156 mmol) of tetrakis(triphenylphosphine)palladium are added andthe mixture is stirred at room temperature for 15 minutes, after which13 ml of 20% strength sodium carbonate solution are added, and stirringis continued at 80° C. for 24 h.

For work-up, the mixture was concentrated, partitioned between aqueouscitric acid and methylene chloride, dried and concentrated. For furtherpurification, the crude product was partitioned between 1N NaOH andmethylene chloride, the aqueous phase was acidified and the precipitatedproduct was filtered off with suction and dried.

Yield: 0.38 g (35% of theory) of a crystalline solid m.p.: 215–217° C.

EXAMPLE I-2-a-5

9.4 ml of 1 M solution of potassium tert-butoxide in DMF are slowlyadded dropwise to 7.82 mmol of the compound of Example (III-1) in 10 mlof DMF, and the mixture is stirred at room temperature overnight. Thesolvent is distilled off, the residue is taken up in water and acidifiedwith dilute hydrochloric acid. The mixture is stirred for another 2hours and then filtered off with suction.

Yield: 2.78 g, m.p. 285–287° C.

By the method of Example (I-2-a-1) and (I-2-a-5), and in accordance withthe general procedures for preparing compounds of the formula (I-2-a)the following compounds of the formula (I-2-a) are obtained:

(I-2-a)

Ex. No. X Z V¹ V² A B m.p. ° C. I-2-a-2 Cl H 4-Cl H—(CH₂)₂—CHOCH₃—(CH₂)₂— 223–225 I-2-a-3 CH₃ Cl 4-Cl H—(CH₂)₂—CHOCH₃—(CH₂)₂— 157–160 I-2-a-4 C₂H₅ CH₃ 4-Cl H—(CH₂)₂—CHOCH₃—(CH₂)₂— 212–215 I-2-a-5 CH₃ CH₃ 4-Cl H CH₃ CH₃ 285–287I-2-a-6 CH₃ CH₃ 4-Cl H —(CH₂)₄— 263–266 I-2-a-7 CH₃ CH₃ 4-Cl H —(CH₂)₅—242–244 I-2-a-8 CH₃ CH₃ 4-Cl H —CH₂—CHCH₃—(CH₂)₃— 221–223 I-2-a-9 CH₃CH₃ 4-Cl H —(CH₂)₂—CHCH₃—(CH₂)₂— 249–251 I-2-a-10 CH₃ CH₃ 4-Cl H—CH₂—O—(CH₂)₃— 255–258 I-2-a-11 CH₃ CH₃ 4-Cl H —(CH₂)₂—O—(CH₂)₂— 274–276I-2-a-12 CH₃ CH₃ 4-Cl H —CH₂—CHCH₃—O—(CH₂)₂— 168–170 I-2-a-13 CH₃ CH₃4-Cl H —(CH₂)₂—CHOC₂H₅(CH₂)₂ 214–217 I-2-a-14 CH₃ CH₃ 4-Cl H

225–228

EXAMPLE I-2-b-1

0.32 g of triethylamine and then 0.33 g of isobutyryl chloride are addedto 1.03 g of the compound of Example I-2-a-5 in 20 ml of methylenechloride. The mixture is stirred overnight and then shaken with diluteaqueous citric acid and 1 N NaOH, and the organic phase is dried andconcentrated. Yield 1.16 g.

¹H NMR (CDCl₃): 1.05 ppm (d, 6H); 1.55 ppm (s, 6H); 2.25 ppm (s, 6H);2.65 ppm (m, 1H), 7.25–7.50 ppm (m, 6H).

By the method of Example (I-2-b-1), and/or in accordance with thegeneral procedures for preparing compounds of the formula (I-2-b) thefollowing compounds of the formula (I-2-b) are obtained:

(I-2-b)

m.p. Ex. No. X Z V¹ V² A B R¹ ° C. I-2-b-2 CH₃ CH₃ 4-Cl H —(CH₂)₄—i-C₃H₇— oil I-2-b-3 CH₃ CH₃ 4-Cl H —(CH₂)₅— i-C₃H₇— oil I-2-b-4 CH₃ CH₃4-Cl H —CH₂—CHCH₃—(CH₂)₃— i-C₃H₇— oil I-2-b-5 CH₃ CH₃ 4-Cl H—(CH₂)₂—CHCH₃—(CH₂)₂— i-C₃H₇— oil I-2-b-6 CH₃ CH₃ 4-Cl H —CH₂—O—(CH₂)₃—i-C₃H₇— oil I-2-b-7 CH₃ CH₃ 4-Cl H —(CH₂)₂—O—(CH₂)₂— i-C₃H₇— oil I-2-b-8CH₃ CH₃ 4-Cl H —CH₂—CHCH₃—O—(CH₂)₂— i-C₃H₇— oil I-2-b-9 CH₃ CH₃ 4-Cl H—(CH₂)₂—CHOC₂H₅—(CH₂)₂— i-C₃H₇— oil

EXAMPLE I-2-c-1

By the method of Example (I-2-b-1), the compound shown above is obtainedstarting from the compound of Example (I-2-a-13) and isopropylchloroformate.

EXAMPLE 1–3-a-1

45.0 g (81 mmol) of the compound of Example (IV-1) in 91 ml oftrifluoroacetic acid and 210 ml of toluene are heated at refluxovernight. The mixture is concentrated and the residue is then taken upin 200 ml of MTBE and 600 ml of water and adjusted to pH 14 by additionof NaOH. The organic phase is added dropwise to 111 of 1N HCl, themixture is stirred for 2 hours, the product is filtered off withsuction, washed with cyclohexane and dried. Yield 18.3 g (57% of theory)m.p.:>250° C.

EXAMPLE I-3-b-1

With ice-cooling, a solution of 0.79 ml of isovaleryl chloride in 3 mlof absolute methylene chloride is added dropwise to 2.0 g of thecompound of Example (I-3-a-1) and 1.04 ml of triethylamine in 15 ml ofabsolute methylene chloride, and the mixture is stirred at roomtemperature for 2 hours. The mixture is washed with 10% strength aqueouscitric acid and extracted with methylene chloride. The organic phase iswashed with 1N NaOH, dried and concentrated. Yield 2.1 g (87% of theory)of an oil.

¹H NMR (400 MHz, CDCl₃):δ=0.9/(dd, 6 H, CH/CH₃)₂, 1.4–2.0 (m, 10H,cyclohexyl) 2.15 (s, 6H, 2×Ar—CH₃), 7.4–7.7 (m, 6H, Ar—H) ppm.

EXAMPLE I-3-c-1

By the method of Example (I-3-b-1) the compound shown above is obtainedby reacting the compound of Example (I-3-a-1) with ethyl chloroformate.Yield 2.1 g (89% of theory). m.p. 167 to 170° C.

EXAMPLE (I-5-a-1)

1.8 g of 4-chlorophenylboronic acid and 266.3 mg ofbis(triphenylphosphine)-palladium(II) chloride are added to 2.6 g of thecompound of Example (I-5-a-1) from WO 97/02 243 in 21 ml ofdimethoxyethane and 18 ml of 1N Na₂CO₃ solution. The mixture is stirredat reflux overnight, acidified with dilute HCl and concentrated. Theresidue is purified by silica gel chromatography (mobile phasecyclohexane/ethyl acetate 4/1→2/1). Yield 2.55 g (89% of theory);m.p.: >250° C.

EXAMPLE (I-5-a-2)

By the method of Example I-5-a-1, the compound shown above is obtainedstarting from the compound of Example (I-5-a-6) from WO 97/02 243. m.p.107–108° C.

EXAMPLE I-7-a-1

1.5 g (4.3 mmol) of the compound of the formula

are dissolved in 10 ml of dimethoxyethane and admixed with 10 ml of 1 MNa₂CO₃ solution. 1.0 g (6.45 mmol) of p-chlorophenylboronic acid andfinally, as catalyst, 254 mg (0.22 mmol) of Pd(PPh₃)₄ (Ph=phenyl) areadded. The mixture is heated at reflux overnight and then filtered, andthe filter cake is rinsed with ethyl acetate. The filtrate is admixedwith water and extracted 3 times each with ethyl acetate and methyltert-butyl ether (MTBE). The combined organic phases are washed withwater and saturated NaCl solution, dried and concentrated.

Crude yield: 1.85 g.

Silica gel column chromatography using cyclohexane/ethyl acetate 15/1gives 100 mg of the compound shown above.

Two other fractions (300 mg and 400 mg) of rotamers of the cis isomerare obtained.

EXAMPLE I-7-a-2

20.5 g of the compound of Example (X-1) in 50 ml of absolute DMF areadmixed with 8.44 g of potassium tert-butoxide and heated at 80° C. for1 hour. With ice-cooling, the mixture is slowly added to 2 l of 1N HCl.The mixture is extracted with methylene chloride and the extract isdried and concentrated. Yield 18 g (95% of theory), m.p.: 192–195° C.

By the method of Example (I-7-a-1) and (I-7-a-2), and/or in accordancewith the general procedures for preparing compounds of the formula(I-7-a) the following compounds of the formula (I-7-a) are obtained:

Ex.- m.p. No. X Z V¹ V² B A Q¹ Q² ° C. I-7-a-3 CH₃ CH₃ 3-Cl H —(CH₂)₅ HH >250 I-7-a-4 CH₃ CH₃ 4-Cl H H —(CH₂)₄— H >250 I-7-a-5 CH₃ CH₃ 3-Cl H H—(CH₂)₄— H 211– 213 I-7-a-6 CH₃ CH₃ 4-Cl H —(CH₂)₃—CHCH₃—CH₂— H H 243–244 I-7-a-7 CH₃ CH₃ 3-Cl H —(CH₂)₃—CHCH₃—CH₂— H H wax

EXAMPLE I-7-b-1

By the method of Example (I-3-b-1), the compound shown above is obtainedby reacting the compound of Example (I-7-a-1) with isobutyryl chloride.m.p.: oil.

¹H NMR (400 MHz; DMSO): δ=0.9–1.0 (d, 6H, HC—CH ₃); 1.2–2.0 (m, 8H,cyclohexyl-H); 2.1 2.15 (s, 6H, 2×ArCH₃); 2.65 (m, 1H, CHCH₃); 7.4 (s,2H, Ar—H); 7.5–7.7 (d, 4H, Ar—H) ppm.

EXAMPLE I-7-b-2

By the method of Example (I-3-b-1) the compound shown above is obtainedas an oil by reacting the compound of Example (I-7-a-5) with isobutyrylchloride.

¹H NMR (400 MHz; DMSO): δ=1–1.1 (d, 6H, CH—CH ₃), 42.0 (m, 8H,cyclohexyl-H); 2.15–2.2 (s, 6H, 2×ArCH₃); 2.6 (m, 1H, CH—CH₃); 2.9–3.4(m, 2H, cyclohexyl C—H); 7.3–7.6 (m, 6H, Ar—H) ppm.

By the method of Example (I-7-b-1), and/or in accordance with thegeneral procedures for preparing compounds of the formula (I-7-b), thefollowing compounds of the formula (I-7-b) are obtained:

Ex. No. X Z V¹ V² B A Q¹ Q² R¹ m.p. ° C. I-7-b-3 CH₃ CH₃ 4-Cl H —(CH₂)₅—H H i-C₄H₉ oil

EXAMPLE I-7-c-1

By the method of Example (I-3-b-1), the compound shown above is obtainedas a wax by reacting the compound of Example (I-7-a-2) with ethylchloroformate.

EXAMPLE 1–8-a-1

6.0 g of the compound of Example (XI-1) are initially charged in 20 mlof DMF, admixed with 2.63 g of potassium tert-butoxide and heated at 80°C. for 1 hour. With ice-cooling, the mixture is then slowly added to 1 lof 1N HCl, and the product is filtered off with suction and dried. Yield5.15 g (93% of theory). m.p.: 222–224° C.

EXAMPLE I-8-a-2

By the method of Example (I-8-a-1),

of m.p. 117–122° C. is obtained.

EXAMPLE 1–8-b-1

By the method of Example (I-3-b-1), the compound shown above is obtainedas an oil by reacting the compound of Example (I-8-a-1) and isovalerylchloride.

¹H NMR (400 MHz; CDCl₃): δ=0.55 (d, 6H, CH(CH ₃)₂), 1.2 (s, 6H, C(CH₃)₂), 1.6 (m, 1H, CH(CH₃)₂), 2.1 (s, 6H, 2×Ar—CH₃), 7.3–7.65 (m, 6H,Ar—H) ppm.

EXAMPLE I-8-b-2

By the method of Example (I-3-6-1), the compound shown above is obtainedas an oil by reacting the compound of Example (I-8-a-2) with isovalerylchloride.

¹H NMR (400 MHz; CDCl₃): δ=0.55 (d, 6H, CH(CH ₃)₂), 1.2 (s, 6H, C(CH₃)₂), 1.6 (m, 1H, CH(CH₃)₂), 2.0;2.7 (t, 2×2H, CH ₂—CH ₂), 2.05 (s, 6H,2×Ar—CH₃), 7.3–7.65 (m, 6H, Ar—H) ppm.

EXAMPLE I-8-c-1

By the method of Example (I-3-b-1), the compound shown above is obtainedas a wax-like substance by reacting the compound of Example (I-8-a-1)with ethyl chloroformate.

¹H NMR (400 MHz; CDCl₃):δ=1.05 (t, 3H, CH₂CH ₃, 1.2 (s, 6H, C(CH₃)₂),2.1 (s, 6H, 2×Ar—CH₃), 2.45;2.7 (s, 2×2H, CH₂), 4.1 (q, 2H, CH ₂—CH3)7.35–7.7 (m, 6H, Ar—H) ppm.

EXAMPLE I-8-c-2

By the method of Example 1-3-b-1, the compound shown above is obtainedas a wax-like substance by reacting the compound of Example (I-8-a-2)with ethyl chloroformate.

¹H NMR (400 MHz; CDCl₃):δ=1.05 (t, 3H, CH₂CH ₃, 1.15 (s, 6H, C(CH₃)₂),2.0; 2.7 (t, 2×2H, CH ₂—CH ₂) 2.05 (s, 6H, Qx, Ar—CH₃), 4.05 (q, 2H, CH₂—CH3) 7.3–7.7 (m, 6H, Ar—H) ppm.

EXAMPLE III-1

At a temperature of from 30 to 40° C., 7.75 g of the compound of ExampleXXIX-1 in 80 ml of methylene chloride are added dropwise to 10.3 g ofconcentrated sulphuric acid, and the mixture is stirred at thistemperature for 2 hours. 14 ml of methanol are then added dropwise, andthe mixture is stirred at 70° C. for a further 6 hours. The mixture isthen poured onto 110 g of ice and extracted with methylene chloride, andthe organic phase is washed with aqueous NaHCO₃ solution, dried andconcentrated. The residue is recrystallized from MTBE/n-hexane and thenpurified further by silica gel column chromatography (mobile phasemethylene chloride/ethyl acetate 5/3). Yield 4.24 g (50% of theory).m.p.: 142° C.

EXAMPLE II-2

At 5–10° C., 5.86 g of 2,6-dimethyl-4-(4-chlorophenyl)-phenylacetylchloride according to Example (XXIV-1) in 10 ml of acetonitrile areadded dropwise to 4.57 g of methyl 3-methyl-1-amino-cyclohexanecarboxylate×hydrochloride and 10 g of ground K₂CO₃ in 20 ml ofacetonitrile, and the mixture is stirred at room temperature for 3hours. The mixture is poured into 200 ml of ice-water and filtered offwith suction, and the residue is taken up in methylene chloride, driedand concentrated. The residue is recrystallized from MTBE/n-hexane.Yield 7.12 g (83% of theory), m.p.: 169° C.

By the method of Examples (II-1) and (II-2), and/or in accordance withthe general procedures for preparing compounds of the formula (II), thefollowing compounds of the formula (II) are obtained:

(II)

Ex.- m.p. No. X Z V¹ V² D A B R⁸ ° C. isomer II-3 CH₃ CH₃ 3-Cl H H—(CH₂)₂—CHOCH₃—(CH₂)₂— CH₃ 88 β II-4 CH₃ CH₃ 4-Cl H H—(CH₂)₂—CHOCH₃—(CH₂)₂— CH₃ 127 β II-5 CH₃ CH₃ 2-Cl H H—(CH₂)₂—CHOCH₃—(CH₂)₂— CH₃ 75 β II-6 CH₃ CH₃ 4-Cl H H —(CH₂)₂—O—(CH₂)₂—CH₃ 179 — II-7 CH₃ CH₃ 4-Cl H H —(CH₂)₂—OCHC₂H₅—(CH₂)₂— CH₃ 146 β II-8CH₃ CH₃ 4-Cl H H —(CH₂)₂—CHCH₃—(CH₂)₂— CH₃ 167 β II-9 CH₃ CH₃ 4-CH₃ H H—(CH₂)₂—CHOCH₃—(CH₂)₂— CH₃ 159 β II-10 CH₃ CH₃ 2-CH₃ 5-F H—(CH₂)₂—CHOCH₃—(CH₂)₂— CH₃ 138 β II-11 CH₃ CH₃ 2-CH₃ 5-CH₃ H—(CH₂)₂—CHOCH₃—(CH₂)₂— CH₃ 71 β II-12 CH₃ CH₃ 2-CH₃ 3-CH₃ H—(CH₂)₂—CHOCH₃—(CH₂)₂— CH₃ 133 β II-13 CH₃ CH₃ 2-OCH₃ H H—(CH₂)₂—CHOCH₃—(CH₂)₂— CH₃ 156 β II-14 CH₃ CH₃ 3-CH₃ 5-CH₃ H—(CH₂)₂—CHOCH₃—(CH₂)₂— CH₃ 169 β II-15 CH₃ CH₃ 2-Cl 4-Cl H—(CH₂)₂—CHOCH₃—(CH₂)₂— CH₃ 125 β II-16 CH₃ CH₃ 2-Cl 3-Cl H—(CH₂)₂—CHOCH₃—(CH₂)₂— CH₃ 127 β II-17 CH₃ CH₃ 4-Cl H —(CH₂)₄— H C₂H₅oil — II-18 CH₃ CH₃ 4-Cl H —(CH₂)₂—S—CH₂— H C₂H₅ 81 — II-19 CH₃ CH₃ 4-ClH i-C₃H₇ H H C₂H₅ 119 —

EXAMPLE XXIX-1

At 5–10° C., 8.79 g of 2,6-dimethyl-4-(4-chlorophenyl)-phenylacetylchloride in 15 ml of acetonitrile are added dropwise to 3.7 g of2-amino-2,3-dimethyl-butyronitrile and 13.8 g of ground K₂CO₃ in 30 mlof acetonitrile, and the mixture is stirred at room temperature for 3hours. The mixture is poured into 250 ml of ice-water and filtered offwith suction, and the residue is washed with water. The residue is takenup in methylene chloride, and the solution is dried and concentrated.The product is subsequently purified by silica gel chromatography(mobile phase n-hexane/ethyl acetate 3/1). Yield 8.24 g (74% of theory),m.p. 180° C.

EXAMPLE (III-1)

The mixture of 2.29 g of the compound of Example (XXIV-1) and 1.03 g ofethyl hydroxyisobutyrate is heated at 140° C. overnight.

GC/MS: m/e=115 (8%), 179 (34%), 229 (100%), 256 (12%), 388 (20%).

By the method of Example (III-1), and/or in accordance with the generalprocedures for preparing compounds of the formula (III), the followingcompounds of the formula (III) are obtained:

(III)

Ex. m.p. No. X Z V¹ V² A B R⁸ ° C. III-2 CH₃ CH₃ 4-Cl H —(CH₂)₄— C₂H₅oil* III-3 CH₃ CH₃ 4-Cl H —(CH₂)₅— C₂H₅ oil* III-4 CH₃ CH₃ 4-Cl H—CH₂—CHCH₃—(CH₂)₃— C₂H₅ oil* III-5 CH₃ CH₃ 4-Cl H —(CH₂)₂—CHCH₃—(CH₂)₂—C₂H₅ oil* III-6 CH₃ CH₃ 4-Cl H —CH₂—O—(CH₂)₃— C₂H₅ oil* III-7 CH₃ CH₃4-Cl H —(CH₂)₂—O—(CH₂)₂— C₂H₅ oil* III-8 CH₃ CH₃ 4-Cl H—CH₂—CHCH₃—O—(CH₂)₂— C₂H₅ oil* III-9 CH₃ CH₃ 4-Cl H—(CH₂)₂—CHOC₂H₅—(CH₂)₂— C₂H₅ oil* III-10 CH₃ CH₃ 4-Cl H

C₂H₅ oil* *The identity was established using GC/MS and the crudeproducts were used directly for preparing the compounds of the formula(I-2-a).

EXAMPLE (IV-1)

-   15.0 g of the compound,

-    9.63 g of thionyl chloride and 1 drop of DMF were stirred at room    temperature for 5 minutes and then at 100° C. until the evolution of    gas had ceased. The mixture is then concentrated and dried under    high vacuum.-   B: At 0° C., 25.3 g of the compound of Example (XXXII-1) are added    dropwise to 45.8 ml (96.3 mmol) of a lithium diisopropylamide (LDA)    solution in 100 ml of absolute tetrahydrofuran (THF), and the    mixture is stirred at this temperature for 30 minutes. The acyl    chloride obtained according to A is then added dropwise in 30 ml of    THF, cooling is removed and the mixture is stirred for another hour.    300 ml of MTBE and a few drops of water are added and the mixture is    washed twice with 300 ml of 10% aqueous ammonium chloride solution    each time, dried and concentrated. Yield 45 g (100% of theory) as an    oil.

¹H NMR (CDCl₃, 400 MHz):δ=1.5–2.0 (m, 10H, cyclohexyl), 2.4 (s, 6H,2×Ar—CH₃), 3.1; 3.3 (d, 2H, S—CH ₂) 3.6; 3.7 (s, 2×3H, 2×OCH₃), 6.8–7.7(m, 10H, Ar—H) ppm.

EXAMPLE X-1

70.0 g of the compound of Example (XXVIII-1), 24.05 g of potassiumcarbonate and 74.4 g of methyl iodide in 400 ml of acetone are stirredunder reflux for 16 hours. The mixture is filtered and the filtrate isconcentrated. The residue is chromatographed over silica gel (mobilephase methylene chloride/petroleum ether 4/1). Yield 20.5 g (41% oftheory) of an oil.

¹H NMR (CDCl₃, 400 MHz):δ=1.3–1.8 (m, 10H, cyclohexyl), 2.2 (s, 6H,2×Ar—CH ₃), 2.95 (s, 2H, CH₂CO), 3.55 (s, 3H, OCH₃), 3.85 (s, 2H,Ar—CH₂), 7.3–7.65 (m, 6H, Ar—H) ppm.

EXAMPLE (XXXVIII-1)

At −15° C., a solution of 51.9 g of the compound of Example (XXXII-1) in80 ml of THF is added dropwise to 100 ml of a solution of LDA (2 molar)and 200 ml of THF, and the mixture is subsequently stirred at 0° C. for1 hour. At −15° C., a solution of 20.2 g of the compound

in 30 ml of THF is then added dropwise. The mixture is stirred at roomtemperature for 2 hours, 300 ml of water and 80 g of ammonium chlorideare added and the mixture is acidified with concentrated HCl. Themixture is extracted with ether and the ether phase is concentrated. Theresidue is boiled under reflux with 200 g of KOH and 660 ml of water for2 days. After cooling, the mixture is acidified with concentrated HCland extracted with ether. The crude oily product which remains afterconcentration is reacted further without any further purification. Yield70 g (100% of theory).

EXAMPLE (XI-1)

36 g of the compound of Example (XLII-1), 13.2 g of potassium carbonateand 40.8 g of methyl iodide in 200 ml of acetone are boiled under refluxfor 16 hours. The mixture is filtered, the filtrate is concentrated andthe residue is purified by silica gel column chromatography (mobilephase methylene chloride/petroleum ether 2/1). Yield 12 g (52% oftheory), oil.

¹H NMR (400 MHz, CDCl₃,):δ=1.05 (s, 6H, C(CH₃)₂, 2.2 (s, 6H, 2×Ar—CH ₃),2.4; 2.7 (s, 2×2H, CO—CH ₂), 3.6 (s, 3H, OCH₃), 3.85 (s, 2H, Ar—CH₂),7.3–7.65 (m, 6H, Ar—H) ppm.

EXAMPLE (XI-2)

By the method of Example (XI-1), the compound shown above is obtained,likewise as an oil.

¹H NMR (400 MHz, CDCl₃,):δ=1.1 (s, 6H, C(CH ₃)₂), 1.75; 2.55 (t, 2×2H,CH₂CH₂), 2.2 (s, 6H, 2×Ar—CH₃), 3.6 (s, 3H, OCH₃), 3.9 (s, 2H, ArCH₂,7.3–7.7 (m, 6H, Ar—H) ppm.

EXAMPLE (XLII-1)

At −15° C., a solution of 27 g of the compound of Example (XXXII-1) in30 ml of THF is added dropwise to 50 ml of a solution of LDA (2 molar)in 100 ml of THF, and the mixture is stirred at 0° C. for 1 hour. At−15° C., a solution of 8.6 g of the compound

in 20 ml of THF is then added dropwise. The mixture is stirred at roomtemperature for 2 hours, after which 150 ml of water and 40 g ofammonium chloride are added, and the mixture is acidified withconcentrated HCl. The mixture is extracted with ether and the etherphase is concentrated. The residue is boiled under reflux with 100 g ofKOH and 330 ml of water for 2 days. After cooling, the mixture isacidified with concentrated HCl and extracted with ether. The crudeproduct (36 g) which remains after concentration is reacted furtherwithout any further purification.

EXAMPLE (LXII-2)

By the method of Example (LXII-1), the compound shown above is obtained.

EXAMPLE XXIV-1

69 g of the acid of Example XXVII-1 are heated with 55 ml of thionylchloride at 70° C. until the evolution of gas has ceased.

Excess thionyl chloride is subsequently removed under reduced pressure.Yield 54.9 g (74% of theory), m.p.: 102° C.

By the method of Example (XXIV-1), and/or in accordance with the generalprocedures for preparing the compounds of the formula (XXIV), thefollowing compounds of the formula (XXIV) are obtained:

(XXIV)

Ex. No. X Z V¹ V² m.p. ° C. XXIV-2 CH₃ CH₃ 3-Cl H * XXIV-3 CH₃ CH₃ 2-ClH * XXIV-4 CH₃ CH₃ 4-CH₃ H * XXIV-5 CH₃ CH₃ 2-CH₃ 5-F * XXIV-6 CH₃ CH₃2-CH₃ 5-CH₃ * XXIV-7 CH₃ CH₃ 2-CH₃ 3-CH₃ * XXIV-8 CH₃ CH₃ 2-OCH₃ H *XXIV-9 CH₃ CH₃ 3-CH₃ 5-CH₃ * XXIV-10 CH₃ CH₃ 2-Cl 4-Cl * XXIV-11 CH₃ CH₃2-Cl 3-Cl * *The acyl chlorides were used without any furtherpurification for the synthesis of compounds of the formula (II).

EXAMPLE (XVII-1)

At room temperature, 6 g of the compound of Example (XXXII-1), 1.2 g oflithium hydroxide, 20 ml of ethanol, 100 ml of water and 100 ml of THFare stirred overnight. The THF is removed under reduced pressure and theaqueous solution that remains is repeatedly extracted with methylenechloride. The aqueous phase is acidified with concentrated HCl and theprecipitated product is filtered off with suction. Yield 5 g (96% oftheory), m.p. 205° C.

By the method of Example (XXVII-1), and/or in accordance with thegeneral procedures for preparing the compounds (XXVII), the followingcompounds of the formula (XXVII) are obtained:

(XXVII)

Ex. No. X Z V¹ V² m.p. ° C. XXVII-2 CH₃ CH₃ 3-Cl H 143 XXVII-3 CH₃ CH₃2-Cl H 129 XXVII-4 CH₃ CH₃ 4-CH₃ H 154 XXVII-5 CH₃ CH₃ 2-CH₃ 5-F 120XXVII-6 CH₃ CH₃ 2-CH₃ 5-CH₃ 141 XXVII-7 CH₃ CH₃ 2-CH₃ 3-CH₃ 155 XXVII-8CH₃ CH₃ 2-OCH₃ H 151 XXVII-9 CH₃ CH₃ 3-CH₃ 5-CH₃ 173 XXVII-10 CH₃ CH₃2-Cl 4-Cl 166 XXVII-11 CH₃ CH₃ 2-Cl 3-Cl 158

EXAMPLE (XXXII-1)

30 g of the compound of Example (XLV-1) are boiled under reflux with19.8 g of 88% strength KOH in 1000 ml of methanol overnight. Aftercooling, the mixture is admixed with 20 ml of concentrated sulphuricacid and boiled under reflux for 1 hour. The solid is filtered off withsuction and washed with methanol. The methanol in the filtrate isremoved under reduced pressure, and the residue is admixed with waterand extracted with methylene chloride. The organic phase is dried andconcentrated. Yield 1 g (10% of theory), oil.

¹H NMR (400 MHz, CDCl₃,):δ=2.38 (s, 6H, Ar—CH ₃), 3.70 (s, 3H, OCH ₃),3.73 (s, 2H, CH ₂), 7.23 (s, 2H ArH), 7.36–7.39 (AA′, BB′, 2H, ArH),7.48–7.51 (AA′, BB′, 2H, Ar—H) ppm.

EXAMPLE (XXXII-2)

Under argon, 6.1 g of 3-chlorophenylboronic acid, 0.15 g ofbis(triphenylphosphine)palladium(II) chloride and 65 ml of 1M Na₂CO₃solution are introduced into 7.68 g of methyl 4-bromo-2,6-dimethylphenylacetate in 85 ml of dimethoxyethane, and the mixture is stirred underreflux overnight. The mixture is diluted with water and extracted withethyl acetate. The organic phase is washed with ammonium chloridesolution, water and saturated sodium chloride solution, dried andconcentrated. Yield 4.3 g (36% of theory), m.p.: 56° C.

By the method of Examples (XXXII-1) and (XXXII-2), and/or in accordancewith the general procedures for preparing the compounds (XXXII), thefollowing compounds of the formula (XXXII) are obtained:

(XXXII)

Ex. No. X Z V¹ V² R⁸ m.p. ° C. XXXII-2 CH₃ CH₃ 3-Cl H CH₃  56 XXXII-3CH₃ CH₃ 2-Cl H CH₃ oil XXXII-4 CH₃ CH₃ 4-CH₃ H CH₃ 137 XXXII-5 CH₃ CH₃2-CH₃ 5-F CH₃ oil XXXII-6 CH₃ CH₃ 2-CH₃ 5-CH₃ CH₃ oil XXXII-7 CH₃ CH₃2-CH₃ 3-CH₃ CH₃ oil XXXII-8 CH₃ CH₃ 2-OCH₃ H CH₃  85 XXXII-9 CH₃ CH₃3-CH₃ 5-CH₃ CH₃ oil XXXII-10 CH₃ CH₃ 2-Cl 4-Cl CH₃ oil XXXII-11 CH₃ CH₃2-Cl 3-Cl CH₃ oil

EXAMPLE XLVI-1

5 g of 4-bromo-2,6-dimethylaniline, 3.88 g of 4-chlorophenylboronic acidand 0.11 g of bis(triphenylphosphine)palladium(II) chloride in 48.8 mlof 1M Na₂CO₃ solution and 65 ml of dimethoxyethane are heated underreflux overnight. The mixture is admixed with water and extracted withethyl acetate. The organic phase is washed with ammonium chloridesolution, water and saturated sodium chloride solution, dried andconcentrated. Yield 4 g (77% of theory), m.p.: 96° C.

1. A compound of the formula (I)

in which X represents halogen, alkyl, alkoxy, alkenyloxy, alkylthio, alkylsulphinyl, alkylsulphonyl, halogenoalkyl, halogenoalkoxy, halogenoalkenyloxy, nitro, cyano or in each case optionally substituted phenyl, phenoxy, phenylthio, phenylalkoxy or phenylalkylthio, Y represents in each case optionally substituted cycloalkyl, aryl, or hetaryl Z represents hydrogen, halogen, alkyl, alkoxy, alkenyloxy, halogenoalkyl, halogenoalkoxy, halogenoalkenyloxy, nitro or cyano, CKE represents

 wherein A represents hydrogen, in each case optionally halogen-substituted alkyl, alkenyl, alkoxyalkyl, polyalkoxyalkyl, alkylthioalkyl, saturated or unsaturated, optionally substituted cycloalkyl in which optionally at least one ring atom is replaced by a heteroatom, or in each case optionally halogen-, alkyl-, halogenoalkyl-, alkoxy-, halogenoalkoxy-, cyano- or nitro-substituted aryl, arylalkyl or hetaryl, D represents hydrogen or an optionally substituted radical selected from the series consisting of alkyl, alkenyl, alkinyl, alkoxyalkyl, polyalkoxyalkyl, alkylthioalkyl, saturated or unsaturated cycloalkyl in which one or more ring members are optionally replaced by heteroatoms, arylalkyl, aryl, hetarylalkyl or hetaryl or A and D together with the atoms to which they are attached represent a saturated or unsaturated cycle which is unsubstituted or substituted in the A,D moiety and which optionally contains at least one further heteroatom, G represents hydrogen (a) or represents one of the groups

 in which E represents a metal ion equivalent or an ammonium ion, L represents oxygen or sulphur, M represents oxygen or sulphur, R¹ represents in each case optionally halogen-substituted alkyl, alkenyl, alkoxyalkyl, alkylthioalkyl, polyalkoxyalkyl or optionally halogen-, alkyl- or alkoxy-substituted cycloalkyl which may be interrupted by at least one heteroatom, in each case optionally substituted phenyl, phenylalkyl, hetaryl, phenoxyalkyl or hetaryloxyalkyl, R² represents in each case optionally halogen-substituted alkyl, alkenyl, alkoxyalkyl, polyalkoxyalkyl or represents in each case optionally substituted cycloalkyl, phenyl or benzyl, R^(3,) R⁴ and R⁵ independently of one another each represent in each case optionally halogen-substituted alkyl, alkoxy, alkylamino, dialkylamino, alkylthio, alkenylthio, cyclo alkylthio and represents optionally substituted phenyl, benzyl, phenoxy or phenylthio, R⁶ and R⁷ independently of one another each represent hydrogen, in each case optionally halogen-substituted alkyl, cycloalkyl, alkenyl, alkoxy, alkoxyalkyl, represent optionally substituted phenyl, represent optionally substituted benzyl, or together with the nitrogen atom to which they are attached represent a cycle which is optionally interrupted by oxygen or sulphur.
 2. A compound of the formula (I) according to claim 1 wherein X represents halogen, C₁–C₆-alkyl, C₁–C₆-halogenoalkyl, C₁–C₆-alkoxy, C₃–C₆-alkenyloxy, C₁–C₆-alkylthio, C₁–C₆-alkylsulphinyl, C₁–C₆-alkylsuiphonyl, C₁–C₆-halogenoalkoxy, C₃–C₆-halogenoalkenyloxy, nitro, cyano or in each case optionally halogen-, C₁–C₆-alkyl-, C₁–C₆-alkoxy-, C₁–C₄-halogenoalkyl-, C₁–C₄-halogenoalkoxy-, nitro- or cyano-substituted phenyl, phenoxy, phenylthio, benzyloxy or benzylthio, Y represents one of the radicals

 wherein V¹ represents hydrogen, halogen, C₁–C₁₂-alkyl, C₁–C₆-alkoxy, C₁–C₄-halogenoalkyl, C₁–C₄-halogenoalkoxy, nitro, cyano or phenyl, phenoxy, phenoxy-C₁–C₄-alkyl, phenyl-C₁–C₄-alkoxy, phenylthio-C₁–C₄-alkyl or phenyl-C₁–C₄-alkylthio, each of which is optionally mono- or poly-substituted by halogen, C₁–C₆-alkyl, C₁–C₆-alkoxy, C₁–C₄-halogenoalkyl, C₁–C₄-halogenoalkoxy, nitro or cyano, V² and V³ independently of one another each represent hydrogen, halogen, C₁–C₆-alkyl, C₁–C₆-alkoxy, C₁–C₄-halogenoalkyl or C₁–C₄-halogeno-alkoxy, Z represents hydrogen, halogen, C₁–C₆-alkyl, C₁–C₆-halogenoalkyl, C₁–C₆-alkoxy, C₁–C₆-halogenoalkoxy, nitro or cyano, CKE represents

 wherein A represents hydrogen or in each case optionally halogen-substituted C₁–C₁₂-alkyl, C₃–C₈-alkenyl, C₁–C₁₀-alkoxy-C₁–C₈-alkyl, poly-C₁–C₈-alkoxy-C₁–C₈-alkyl, C₁–C₁₀-alkylthio-C₁–C₆-alkyl, optionally halogen-, C₁–C₆-alkyl- or C₁–C₆-alkoxy-substituted C₃–C₈-cycloalkyl in which optionally one or two not directly adjacent ring members are replaced by oxygen and/or sulphur or represents in each case optionally halogen-, C₁–C₆-alkyl-, C₁–C₆-halogenoalkyl-, C₁–C₆-alkoxy-, C₁–C₆-halogenoalkoxy-, cyano- or nitro-substituted C₆- or C₁₀-aryl, hetaryl having 5 to 6 ring atoms or C₆- or C₁₀-aryl-C₁–C₆-alkyl, D represents hydrogen, in each case optionally halogen-substituted C₁–C₁₂-alkyl, C₃–C₈-alkenyl, C₃–C₈-alkinyl, C₁–C₁₀-alkoxy-C₂–C₈-alkyl, poly-C₁–C₈-alkoxy-C₂–C₈-alkyl, C₁–C₁₀-alkylthio-C₂–C₈-alkyl, optionally halogen-, C₁–C₄-alkyl-, C₁–C₄-alkoxy- or C₁–C₄-halogen-oalkyl-substituted C₃–C₈-cycloalkyl in which optionally one ring member is replaced by oxygen or sulphur or in each case optionally halogen-, C₁–C₆-alkyl-, C₁–C₆-halogenoalkyl-, C₁–C₆-alkoxy-, C₁–C₆-halogenoalkoxy-, cyano- or nitro-substituted phenyl, hetaryl having 5 or 6 ring atoms, phenyl-C₁–C₆-alkyl or hetaryl-C₁–C₆-alkyl having 5 or 6 ring atoms, or A and D together represent in each case optionally substituted C₃–C₆-alkane-diyl or C₃–C₆-alkenediyl in which optionally one methylene group is replaced by oxygen or sulphur, possible substituents in each case being: halogen, hydroxyl, mercapto or in each case optionally halogen-substituted C₁–C₁₀-alkyl, C₁–C₆-alkoxy, C₁–C₆-alkylthio, C₃–C₇-cycloalkyl, phenyl or benzyloxy, or a further C₃–C₆-alkanediyl grouping, C₃–C₆-alkenediyl grouping or a butadienyl grouping which is optionally substituted by C₁–C₆-alkyl or in which optionally two adjacent substituents together with the carbon atoms to which they are attached form a further saturated or unsaturated cycle having 5 or 6 ring atoms which cycle may contain oxygen or sulphur, or which may optionally contain one of the groups below

G represents hydrogen (a) or represents one of the groups

 in which E represents a metal ion or an ammonium ion, L represents oxygen or sulphur and M represents oxygen or sulphur, R¹ represents in each case optionally halogen-substituted C₁–C₂₀-alkyl, C₂–C₂₀-alkenyl, C₁–C₈-alkoxy-C₁–C₈-alkyl, C₁–C₈-alkylthio-C₁–C₈-alkyl, poly-C₁–C₈-alkoxy-C₁–C₈-alkyl or optionally halogen-, C₁–C₆-alkyl- or C₁–C₆-alkoxy-substituted C₃–C₈-cycloalkyl in which optionally one or more not directly adjacent ring members are replaced by oxygen and/or sulphur, represents optionally halogen-, cyano-, nitro-, C₁–C₆-alkyl-, C₁–C₆-alkoxy-, C₁–C₆-halogenoalkyl-, C₁–C₆-halogenoalkoxy-, C₁–C₆-alkylthio- or C₁–C₆-alkylsulphonyl-substituted phenyl, represents optionally halogen-, nitro-, cyano-, C₁–C₆-alkyl-, C₁–C₆-alkoxy-, C₁–C₆-halogenoalkyl- or C₁–C₆-halogenoalkoxy-substituted phenyl-C₁–C₆-alkyl, represents optionally halogen- or C₁–C₆-alkyl-substituted 5- or 6-membered hetaryl, represents optionally halogen- or C₁–C₆-alkyl-substituted phenoxy-C₁–C₆-alkyl or represents optionally halogen-, amino- or C₁–C₆-alkyl-substituted 5- or 6-membered hetaryloxy-C₁–C₆-alkyl, R² represents in each case optionally halogen-substituted C₁–C₂₀-alkyl, C₂–C₂₀-alkenyl, C₁–C₈-alkoxy-C₂–C₈-alkyl, poly-C₁–C₈-alkoxy-C₂–C₈-alkyl, represents optionally halogen-, C₁–C₆-alkyl- or C₁–C₆-alkoxy-substituted C₃–C₈-cycloalkyl or represents in each case optionally halogen-, cyano-, nitro-, C₁–C₆-alkyl-, C₁–C₆-alkoxy-, C₁–C₆-halogenoalkyl- or C₁–C₆-halogenoalkoxy-substituted phenyl or benzyl, R³ represents optionally halogen-substituted C₁–C₈-alkyl or represents in each case optionally halogen-, C₁–C₆-alkyl-, C₁–C₆-alkoxy-, C₁–C₄-halogenoalkyl-, C₁–C₄-halogenoalkoxy-, cyano- or nitro-substituted phenyl or benzyl, R⁴ and R⁵ independently of one another each represent in each case optionally halogen-substituted C₁–C₈-alkyl, C₁–C₈-alkoxy, C₁–C₈-alkylamino, di-(C₁–C₈-alkyl)amino, C₁–C₈-alkylthio, C₂–C₈-alkenylthio, C₃–C₇-cycloalkylthio or represent in each case optionally halogen-, nitro-, cyano-, C₁–C₄-alkoxy-, C₁–C₄-halogenoalkoxy-, C₁–C₄-alkylthio-, C₁–C₄-halogenoalkylthio-, C₁–C₄-alkyl- or C₁–C₄-halogenoalkyl-substituted phenyl, phenoxy or phenylthio, R⁶ and R⁷ independently of one another each represent hydrogen, represent in each case optionally halogen-substituted C₁–C₈-alkyl, C₃–C₈-cycloalkyl, C₁–C₈-alkoxy, C₃–C₈-alkenyl, C₁–C₈-alkoxy-C₁–C₈-alkyl, represent optionally halogen-, C₁–C₈-halogenoalkyl-, C₁–C₈-alkyl- or C₁–C₈-alkoxy-substituted phenyl, optionally halogen-, C₁–C₈-alkyl-, C₁–C₈-halogenoalkyl- or C₁–C₈-alkoxy-substituted benzyl or together represent an optionally C₁–C₄-alkyl-substituted C₃–C₆-alkylene radical in which optionally one carbon atom is replaced by oxygen or sulphur, R¹³ represents hydrogen, represents in each case optionally halogen-substituted C₁–C₈-alkyl or C₁–C₈-alkoxy, represents optionally halogen-, C₁–C₄-alkyl- or C₁–C₄-alkoxy-substituted C₃–C₈-cycloalkyl in which optionally one methylene group is replaced by oxygen or sulphur, or represents in each case optionally halogen-, C₁–C₆-alkyl-, C₁–C₆-alkoxy-, C₁–C₄-halogenoalkyl-, C₁–C₄-halogenoalkoxy-, nitro- or cyano-substituted phenyl, phenyl-C₁–C₄-alkyl or phenyl-C₁–C₄-alkoxy, R¹⁴ represents hydrogen or C₁–C₈-alkyl, or R¹³ and R¹⁴ together represent C₄–C₆-alkanediyl, R¹⁵ and R¹⁶ are identical or different and each represent C₁–C₆-alkyl, or R¹⁵ and R¹⁶ together represent a C₂–C₄-alkanedjyl radical which is optionally substituted by C₁–C₆-alkyl, C₁–C₆-halogenoalkyl or by optionally halogen-, C₁–C₆-alkyl-, C₁–C₄-halogenoalkyl-, C₁–C₆-alkoxy-, C₁–C₄-halogenoalkoxy-, nitro- or cyano-substituted phenyl, R¹⁷ and R¹⁸ independently of one another each represent hydrogen, represent optionally halogen-substituted C₁–C₈-alkyl or represent optionally halogen-, C₁–C₆-alkyl-, C₁–C₆-alkoxy-, C₁–C₄-halogenoalkyl-, C₁–C₄-halogenoalkoxy-, nitro- or cyano-substituted phenyl, or R¹⁷ and R¹⁸ together with the carbon atom to which they are attached represent a carbonyl group or represent optionally halogen-, C₁–C₄-alkyl- or C₁–C₄-alkoxy-substituted C₅–C₇-cycloalkyl in which optionally one methylene group is replaced by oxygen or sulphur and R¹⁹ and R²⁰ independently of one another each represent C₁–C₁₀-alkyl, C₂–C₁₀-alkenyl, C₁–C₁₀-alkoxy, C₁–C₁₀-alkylamino, C₃–C₁₀-alkenylamino, di-(C₁–C₁₀-alkyl)amino or di-(C₃–C₁₀-alkenyl)amino.
 3. A compound of the formula (I) according to claim 1 wherein X represents fluorine, chlorine, bromine, C₁–C₄-alkyl, C₁–C₄-alkoxy, C₃–C₄-alkenyloxy, C₁–C₄-halogenoalkyl, C₁–C₄-halogenoalkoxy, C₃–C₄-halogenoalkenyloxy, nitro or cyano, Y represents

 wherein V¹ represents hydrogen, fluorine, chlorine, bromine, C₁–C₆-alkyl, C₁–C₄-alkoxy, C₁–C₂-halogenoalkyl, C₁–C₂-halogenoalkoxy, nitro, cyano or phenyl, phenoxy, phenoxy-C₁–C₂-alkyl, phenyl-C₁–C₂-alkoxy, phenylthio-C₁–C₂-alkyl or phenyl-C₁–C₂-alkylthio, each of which is optionally mono- or disubstituted by fluorine, chlorine, bromine, C₁–C₄-alkyl, C₁–C₄-alkoxy, C₁–C₂-halogenoalkyl, C₁–C₂-halogenoalkoxy, nitro or cyano, V² and V³ independently of one another represents hydrogen, fluorine, chlorine, bromine, C₁–C₄-alkyl, C₁–C₄-alkoxy, C₁–C₂-halogenoalkyl or C₁–C₂-halogenoalkoxy, Z represents hydrogen, fluorine, chlorine, bromine, C₁–C₄-alkyl, C₁–C₄-halogenoalkyl, C₁–C₄-alkoxy or C₁–C₄-halogenoalkoxy, CKE represents

 wherein A represents hydrogen, in each case optionally fluorine- or chlorine-substituted C₁–C₁₀-alkyl, C₁–C₈-alkoxy-C₁–C₆-alkyl, optionally fluorine-, chlorine-, C₁–C₄-alkyl- or C₁–C₄-alkoxy-substituted C₃–C₇-cycloalkyl in which optionally one ring member is replaced by oxygen or sulphur or in each case optionally fluorine-, chlorine-, bromine-, C₁–C₄-alkyl-, C₁–C₄-halogenoalkyl-, C₁–C₄-alkoxy- or C₁–C₄-halogenoalkoxy-substituted phenyl, furanyl, pyridyl, im idazolyl, triazolyl, pyrazolyl, pyrimidyl, thiazolyl, thienyl or phenyl-C₁–C₄-alkyl, D represents hydrogen, represents in each case optionally substituted C₁–C₁₀-alkyl, or substituted C₃–C₇-cycloalkyl in which optionally one methylene group is replaced by oxygen or sulphur. A and D together represent optionally substituted C₃–C₅-alkanediyl in which one methylene group may be replaced by a carbonyl group, oxygen or sulphur, possible substituents being hydroxyl, C₁–C₆-alkyl or C₁–C₄-alkoxy, G represents hydrogen (a) or represents one of the groups

 in which E represents a metal ion or an ammonium ion, L represents oxygen or sulphur and M represents oxygen or sulphur, R¹ represents in each case optionally fluorine- or chlorine-substituted C₁–C₁₆-alkyl, C₂–C₁₆-alkenyl, C₁–C₆-alkoxy-C₁–C₆-alkyl, C₁–C₆-alkylthio-C₁–C₆-alkyl, poly-C₁–C₆-alkoxy-C₁–C₆-alkyl or optionally fluorine-, chlorine-, C₁–C₅-alkyl- or C₁–C₅-alkoxy-substituted C₃–C₇-cycloalkyl in which optionally one or two not directly adjacent ring members are replaced by oxygen and/or sulphur, represents optionally fluorine-, chlorine-, bromine-, cyano-, nitro-, C₁–C₄-alkyl-, C₁–C₄-alkoxy-, C₁–C₃-halogenoalkyl-, C₁–C₃-halogenoalkoxy-, C₁–C₄-alkylthio- or C₁–C₄-alkylsulphonyl-substituted phenyl, represents optionally fluorine-, chlorine-, bromine-, C₁–C₄-alkyl-, C₁–C₄-alkoxy-, C₁–C₃-halogenoalkyl- or C₁–C₃-halogenoalkoxy-substituted phenyl-C₁–C₄-alkyl, represents in each case optionally fluorine-, chlorine-, bromine- or C₁–C₄-alkyl-substituted pyrazolyl, thiazolyl, pyridyl, pyrimidyl, furanyl or thienyl, represents optionally fluorine-, chlorine-, bromine- or C₁–C₄-alkyl-substituted phenoxy-C₁–C₃-alkyl or represents in each case optionally fluorine-, chlorine-, bromine-, amino- or C₁–C₄-alkyl-substituted pyridyloxy-C₁–C₃-alkyl, pyrimidyloxy-C₁–C₃-alkyl or thiazolyloxy-C₁–C₃-alkyl, R² represents in each case optionally fluorine-substituted C₁–C₁₆-alkyl, C₂–C₁₆-alkenyl, C₁–C₆-alkoxy-C₂–C₆-alkyl or poly-C₁–C₆-alkoxy-C₂–C₆-alkyl, represents optionally fluorine-, chlorine-, C₁–C₄-alkyl- or C₁–C₄-alkoxy-substituted C₃–C₇-cycloalkyl or represents in each case optionally fluorine-, chlorine-, bromine-, cyano-, nitro-, C₁–C₄-alkyl-, C₁–C₃-alkoxy-, C₁–C₃-halogenoalkyl- or C₁–C₃-halogenoalkoxy-substituted phenyl or benzyl, R³ represents optionally fluorine-substituted C₁–C₆-alkyl or represents in each case optionally fluorine-, chlorine-, bromine-, C₁–C₄-alkyl-, C₁–C₄-alkoxy-, C₁–C₃-halogenoalkyl-, C₁–C₃-halogenoalkoxy-, cyano- or nitro-substituted phenyl or benzyl, R⁴ and R⁵ independently of one another each represent C₁–C₆-alkyl, C₁–C₆-alkoxy, C₁–C₆-alkylamino, di-(C₁–C₆-alkyl)amino, C₁–C₆-alkylthio, C₃–C₄-alkenylthio, C₃–C₆-cycloalkylthio or represent in each case optionally fluorine-, chlorine-, bromine-, nitro-, cyano-, C₁–C₃-alkoxy-, C₁–C₃-halogenoalkoxy-, C₁–C₃-alkylthio-, C₁–C₃-halogenoalkylthio-, C₁–C₃-alkyl- or C₁–C₃-halogenoalkyl-substituted phenyl, phenoxy or phenylthio, and R⁶ and R⁷ independently of one another each represent hydrogen, C₁–C₆-alkyl, C₃–C₆-cycloalkyl, C₁–C₆-alkoxy, C₃–C₆-alkenyl, C₁–C₆-alkoxy-C₁–C₆-alkyl, represent optionally fluorine-, chlorine-, bromine-, C₁–C₃-halogenoalkyl-, C₁–C₄-alkyl- or C₁–C₄-alkoxy-substituted phenyl, represent optionally fluorine-, chlorine-, bromine-, C₁–C₄-alkyl-, C₁–C₃-halogenoalkyl- or C₁–C₄-alkoxy-substituted benzyl, or together represent an optionally methyl- or ethyl-substituted C₄–C₅-alkylene radical in which optionally one methylene group is replaced by oxygen or sulphur.
 4. A compound of the formula (I) according to claim 1 wherein X represents fluorine, chlorine, methyl, ethyl, propyl, iso-propyl, methoxy, ethoxy, propoxy, iso-propoxy, trifluoromethyl, difluoromethoxy, trifluoromethoxy, nitro or cyano, Y represents

 wherein V¹ represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, tert-butyl, methoxy, ethoxy, n-propoxy, iso-propoxy, trifluoromethyl, trifluoromethoxy, nitro, cyano or phenyl, V² and V³ independently of one another each represents hydrogen, fluorine, chlorine, methyl, ethyl, n-propyl, iso-propyl, methoxy, ethoxy, trifluoromethyl or trifluoromethoxy, Z represents hydrogen, fluorine, chlorine, methyl, ethyl, n-propyl, methoxy, ethoxy or n-propoxy, CKE represents

 wherein A represents hydrogen, in each case optionally fluorine-substituted C₁–C₈-alkyl or C₁–C₆-alkoxy-C₁–C₄-alkyl, optionally fluorine-, methyl-, ethyl- or methoxy-substituted C₃–C₆-cycloalkyl in which optionally one ring member is replaced by oxygen or sulphur or represents in each case optionally fluorine-, chlorine-, bromine-, methyl-, ethyl-, n-propyl-, iso-propyl-, methoxy-, ethoxy-, trifluoromethyl-, trifluoromethoxy-, cyano- or nitro-substituted phenyl or benzyl, D represents hydrogen, represents in each case optionally fluorine- or chlorine-substituted C₁–C₈-alkyl, C₃–C₄-alkenyl, C₁–C₆-alkoxy-C₂–C₄-alkyl, C₁–C₄-alkylthio-C₂–C₄-alkyl or C₃–C₆-cycloalkyl in which optionally one methylene group is replaced by oxygen or sulphur or (but not in the case of the compounds of the formulae (I-1) and (I-4)) represents in each case optionally fluorine-, chlorine-, methyl-, ethyl-, n-propyl-, iso-propyl-, methoxy-, ethoxy-, trifluoromethyl- or trifluoromethoxy-substituted phenyl, furanyl, pyridyl, thienyl or benzyl,  or A and D together represent optionally substituted C₃–C₄-alkanediyl in which optionally one carbon atom is replaced by sulphur and which is optionally substituted by hydroxyl, methyl, ethyl, methoxy or ethoxy, G represents hydrogen (a) or represents one of the groups

 in which E represents a metal ion or an ammonium ion, L represents oxygen or sulphur and M represents oxygen or sulphur, R¹ represents in each case optionally fluorine- or chlorine-substituted C₁–C₁₄-alkyl, C₂–C₁₄-alkenyl, C₁–C₄-alkoxy-C₁–C₆-alkyl, C₁–C₄-alkylthio-C₁–C₆-alkyl, poly-C₁–C₄-alkoxy-C₁–C₄-alkyl or optionally fluorine-, chlorine-, methyl-, ethyl-, n-propyl-, i-propyl-, n-butyl-, i-butyl-, tert-butyl-, methoxy-, ethoxy-, n-propoxy- or iso-propoxy-substituted C₃–C₆-cycloalkyl in which optionally one or two not directly adjacent ring members are replaced by oxygen and/or sulphur, represents optionally fluorine-, chlorine-, bromine-, cyano-, nitro-, methyl-, ethyl-, n-propyl-, i-propyl-, methoxy-, ethoxy-, trifluoromethyl-, trifluoromethoxy-, methylthio-, ethylthio-, methylsulphonyl- or ethylsulphonyl-substituted phenyl, represents optionally fluorine-, chlorine-, bromine-, methyl-, ethyl-, n-propyl-, i-propyl-, methoxy-, ethoxy-, trifluoromethyl- or trifluoro-methoxy-substituted benzyl, represents in each case optionally fluorine-, chlorine-, bromine-, methyl- or ethyl-substituted furanyl, thienyl, pyridyl, pyrimidyl, thiazolyl or pyrazolyl, represents optionally fluorine-, chlorine-, methyl- or ethyl-substituted phenoxy-C₁–C₂-alkyl or represents in each case optionally fluorine-, chlorine-, amino-, methyl- or ethyl-substituted pyridyloxy-C₁–C₂-alkyl, pyrimidyloxy-C₁–C₂-alkyl or thiazolyloxy-C₁–C₂-alkyl, R² represents in each case optionally fluorine-substituted C₁–C₁₄-alkyl, C₂–C₁₄-alkenyl, C₁–C₄-alkoxy-C₂–C₆-alkyl or poly-C₁–C₄-alkoxy-C₂–C₆-alkyl, represents optionally fluorine-, chlorine-, methyl-, ethyl-, n-propyl-, isopropyl- or methoxy-substituted C₃–C₆-cycloalkyl, or represents in each case optionally fluorine-, chlorine-, cyano-, nitro-, methyl-, ethyl-, n-propyl-, i-propyl-, methoxy-, ethoxy-, trifluoromethyl- or trifluoromethoxy-substituted phenyl or benzyl, R³ represents in each case optionally fluorine-substituted methyl, ethyl, n-propyl, isopropyl or in each case optionally fluorine-, chlorine-, bromine-, methyl-, tert-butyl-, methoxy-, trifluoromethyl-, trifluoromethoxy-, cyano- or nitro-substituted phenyl or benzyl, R⁴ and R⁵ independently of one another each represent C₁–C₄-alkyl, C₁–C₄-alkoxy, C₁–C₄-alkylamino, di-(C₁–C₄-alkyl)amino, C₁–C₄-alkylthio or represent in each case optionally fluorine-, chlorine-, bromine-, nitro-, cyano-, C₁–C₂-alkoxy-, C₁–C₂-fluoroalkoxy-, C₁–C₂-alkylthio-, C₁–C₂-fluoroalkylthio- or C₁–C₃-alkyl-substituted phenyl, phenoxy or phenylthio, and R⁶ and R⁷ independently of one another each represent hydrogen, represent C₁–C₄-alkyl, C₃–C₆-cycloalkyl, C₁–C₄-alkoxy, C₃–C₄-alkenyl, C₁–C₄-alkoxy-C₁–C₄-alkyl, represent optionally fluorine-, chlorine-, bromine-, trifluoromethyl-, methyl- or methoxy-substituted phenyl, represent optionally fluorine-, chlorine-, bromine-, methyl-, trifluoromethyl- or methoxy-substituted benzyl, or together represent a C₅–C₆-alkylene radical in which optionally one methylene group is replaced by oxygen or sulphur.
 5. A process for preparing a compound of the formula (I) according to claim 1, comprising (D) when said compound of the formula (I) is a compound of the formula (I-4-a)

 in which A, D, X, Y and Z are each as defined in claim 1, reacting (Dα) halogenocarbonyl ketenes of the formula (V)

 in which X, Y and Z are each as defined above and Hal represents halogen, or by (Cβ) reacting a malonic acid derivative of the formula (VI)

 in which R⁸ represents alkyl, X,Y and Z are each as defined above, with a hydrazine of the formula (VII) A-NH—NH-D  (VII)  in which A and D are each as defined above, optionally in the presence of a diluent and optionally in the presence of a base, or (I) when said compound of the formula (I) is a compound of the formula (I-4-a) defined above, reacting a compound of the formula (I-4′-a),

 in which A, D, X and Z are each as defined above and Y′ represents chlorine, bromine or iodine with a boronic acid of the formula (XII)

 in which Y is as defined above, in the presence of a solvent, a base and a catalyst, or (J) when said compound of the formula (I) is a compound of the formula (I-4-b)

 in which A, D, R¹, X, Y and Z are each as defined in claim 1, (Jα) reacting a compound of the formula (I-4-a) above in which A, D, X Y and Z are each as defined above with an acyl halide of the formula (XIII).

 in which R¹ is as defined above and Hal represents halogen or (Jβ) reacting a compound of the formula (I-4-a) above in which A, D, X Y and Z are each as defined above with a carboxylic anhydride of the formula (XIV) R¹—CO—O—CO—R¹(XIV)  in which R¹ is as defined above, optionally in the presence of a diluent and optionally in the presence of an acid binder, or (K) when said compound of the formula (I) is a compound of the formula (I-4-c)

 in which A, D, R², M, X, Y and Z are each as defined in claim 1 and L represents oxygen, reacting a compound of the formula (I-4-a) above in which A, D, X Y and Z are each as defined above with a chioroformic ester or a chioroformic thioester of the formula (XV) R²-M-CO—Cl  (XV)  in which R² and M are each as defined above, optionally in the presence of a diluent and optionally in the presence of an acid binder, or (L) when the compound of the formula (I) is a compound of the formula (I-4-c) defined above in which A, D, R², M, X,Y and Z are each as defined above and L represents sulphur, reacting a compound of the formula (I-4-a) defined above in which A, D, X, Y and Z are each as defined above with a chloromonothioformic ester or a chlorodithioformic ester of the formula (XVI)

 in which M and R² are each as defined above, optionally in the presence of a diluent and optionally in the presence of an acid binder, or (M) when the compound of the formula (I) is a compound of the formula (I-4-d)

 in which A, D, R³, X, Y and Z are each as defined in claim 1, reacting a compound of the formula (I-4-a) defined above in which A, D, X, Y and Z are each as defined above with a suiphonyl chloride of the formula (XVII) R³—SC₂—CI  (XVII)  in which R³ is as defined above, optionally in the presence of a diluent and optionally in the presence of an acid binder, or (N) when the compound of the formula (I) is a compound of the formula (I-4-e)

 in which A, D, L, R⁴, R⁵, X, Y and Z are each as defined in claim 1, reacting a compound of the formula (I-4-a) defined above in which A, D, X, Y and Z are each as defined above with a phosphorus compound of the formula

 in which L, R⁴ and R⁵ are each as defined above and Hal represents halogen, optionally in the presence of a diluent and optionally in the presence of an acid binder, or (O) when the compound of the formula (I) is a compound of the formula (I-4-f)

 in which A, D, E, X, Y and Z are each as defined in claim 1, reacting a compound of the formula (I-4-a) defined above in which A, D, X, Y and Z are each as defined above with a with metal compound or amine of the formulae (XIX) or (XX) Me(OR¹⁰)_(t)  (XIX)

 in which Me represents a mono- or divalent metal, t represents the number 1 or 2 and R¹⁰, R¹¹, R¹² independently of one another each represent hydrogen or alkyl, optionally in the presence of a diluent, or (P) when the compound of the formula (I) is a compound of the formula (I-4-g)

 wherein A, D, L, R⁶, R⁷, X, Y and Z are each as defined in claim 1, (Pα) reacting a compound of the formula (I-4-a) defined above in which A, D, X, Y and Z are each as defined above with an isocyanate or an isothiocyanate of the formula (XXI) R⁶—N═C=L  (XXI)  in which R⁶ and L are each as defined above, optionally in the presence of a diluent and optionally in the presence of a catalyst, or (Pβ) reacting a compound of the formula (I-4-a) defined above in which A, D, X, Y and Z are each as defined above with a carbamoyl chioridesor thiocarbamoyl chloride of the formula (XXII)

 in which L, R⁶ and R⁷ are each as defined above, optionally in the presence of a diluent and optionally in the presence of an acid binder.
 6. A pesticide and/or herbicide, comprising at least one compound of the formula (I) according to claim
 1. 7. A method for controlling pests comprising the step of applying an effective amount of a compound of the formula (I) according to claim 1 to a member selected from the group consisting of said pests, a habitat for said pests, and combinations thereof.
 8. A method for preparing a pesticide and/or a herbicide, comprising the step of mixing a compound of the formula (I) according to claim 1 with a member selected from the group consisting of an extender, a surfactant and combinations thereof. 